Unnamed: 0
int64 0
445k
| level_0
int64 0
1.94M
| index
float64 0
1.81M
⌀ | original_rxn
stringlengths 104
2.67k
| fragments
stringlengths 6
161
⌀ | source
stringlengths 11
26
| year
int64 1.98k
2.02k
| mapped_rxn
stringlengths 110
2.63k
| confidence
float64 0
1
| canonical_rxn_with_fragment_info
stringlengths 25
599
| canonical_rxn
stringlengths 25
599
| ID
stringlengths 17
32
| reaction_hash
stringlengths 56
56
| reactants
stringlengths 55
1.33k
| products
stringlengths 51
1.3k
| retro_template
stringlengths 46
417
| template_hash
stringclasses 1k
values | selectivity
float64 0
1
| outcomes
float64 1
15
| reagents
stringlengths 1
370
⌀ | labels
int64 0
999
|
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
219,500 | 737,711 | 1,215,042 | C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[C@H:23]([CH2:24][OH:25])[C@@H:22]2[CH2:26][C@H:19]1[CH2:20][CH2:21]2)=[O:17])([CH3:14])([CH3:13])[CH3:12].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[C@H:23]([CH:24]=[O:25])[C@@H:22]2[CH2:26][C@H:19]1[CH2:20][CH2:21]2)=[O:17])([CH3:14])([CH3:12])[CH3:13] | null | US08236801B2_0504 | 2,012 | CCN(C(C)C)C(C)C.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]([CH2:10][OH:11])[C@H:12]2[CH2:13][CH2:14][C@@H:15]1[CH2:16]2>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]([CH:10]=[O:11])[C@H:12]2[CH2:13][CH2:14][C@@H:15]1[CH2:16]2 | 0.356408 | CC(C)(C)OC(=O)N1[C@H](CO)[C@H]2CC[C@@H]1C2.CCN(C(C)C)C(C)C.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CC(C)(C)OC(=O)N1[C@H](C=O)[C@H]2CC[C@@H]1C2 | CC(C)(C)OC(=O)N1[C@H](CO)[C@H]2CC[C@@H]1C2.CCN(C(C)C)C(C)C.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CC(C)(C)OC(=O)N1[C@H](C=O)[C@H]2CC[C@@H]1C2 | US08236801B2_0504grants | 75686749d7dd0ce9c14eceef1259476369bfadaf5f87edca6c03d00f | CCN(C(C)C)C(C)C.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]([CH2:10][OH:11])[C@H:12]2[CH2:13][CH2:14][C@@H:15]1[CH2:16]2 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[C@H:9]([CH:10]=[O:11])[C@H:12]2[CH2:13][CH2:14][C@@H:15]1[CH2:16]2 | ([#7:1]-[C:2]-[CH;D2;+0:3]=[O;H0;D1;+0:4])>>([#7:1]-[C:2]-[CH2;D2;+0:3]-[OH;D1;+0:4]) | c86f8c1ecc9dec943b561a028f76c22d6bfcd200e6fbdb751c2517af | 1 | 1 | CCN(C(C)C)C(C)C.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl | 610 |
245,329 | 816,307 | 1,351,502 | [CH2:1]([C:3]1[S:29][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][C:15]=3[F:28])[C:8](=[O:12])[NH:9][C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[CH:30]([O:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)([CH3:32])[CH3:31].C(N(CC)CC)C.N1C=CC=CC=1>ClCCl.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([C:3]1[S:29][C:6]2[N:7]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[C:21]([C:26]#[N:27])=[CH:22][CH:23]=[CH:24][CH:25]=4)=[CH:16][C:15]=3[F:28])[C:8](=[O:12])[N:9]([C:37]3[CH:38]=[CH:39][C:34]([O:33][CH:30]([CH3:32])[CH3:31])=[CH:35][CH:36]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2] | |f:6.7.8| | US08501750B2_1304 | 2,013 | CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CCOC(C)=O.ClCCl.OB(O)[c:9]1[cH:10][cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][c:19](=[O:20])[n:21]([CH2:22][c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]4[C:33]#[N:34])[cH:35][c:36]3[F:37])[c:38]2[s:39]1.[Cu+2].c1ccncc1>>[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8](-[c:9]3[cH:10][cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[n:21]([CH2:22][c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]4[C:33]#[N:34])[cH:35][c:36]3[F:37])[c:38]2[s:39]1 | 0.704481 | CC(=O)[O-]~CC(=O)[O-]~[Cu+2].CC(C)Oc1ccc(B(O)O)cc1.CCN(CC)CC.CCOC(C)=O.CCc1cc2c(=O)[nH]c(=O)n(Cc3ccc(-c4ccccc4C#N)cc3F)c2s1.ClCCl.c1ccncc1>>CCc1cc2c(=O)n(-c3ccc(OC(C)C)cc3)c(=O)n(Cc3ccc(-c4ccccc4C#N)cc3F)c2s1 | CC(=O)[O-].CC(=O)[O-].CC(C)Oc1ccc(B(O)O)cc1.CCN(CC)CC.CCOC(C)=O.CCc1cc2c(=O)[nH]c(=O)n(Cc3ccc(-c4ccccc4C#N)cc3F)c2s1.ClCCl.[Cu+2].c1ccncc1>>CCc1cc2c(=O)n(-c3ccc(OC(C)C)cc3)c(=O)n(Cc3ccc(-c4ccccc4C#N)cc3F)c2s1 | US08501750B2_1304grants | 1134a31909d4d7ef13f4e03796059ab72aed4d070688c12ae4e106f2 | CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CCOC(C)=O.ClCCl.OB(O)[c:9]1[cH:10][cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]1.[CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[nH:8][c:19](=[O:20])[n:21]([CH2:22][c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]4[C:33]#[N:34])[cH:35][c:36]3[F:37])[c:38]2[s:39]1.[Cu+2].c1ccncc1 | [CH3:1][CH2:2][c:3]1[cH:4][c:5]2[c:6](=[O:7])[n:8](-[c:9]3[cH:10][cH:11][c:12]([O:13][CH:14]([CH3:15])[CH3:16])[cH:17][cH:18]3)[c:19](=[O:20])[n:21]([CH2:22][c:23]3[cH:24][cH:25][c:26](-[c:27]4[cH:28][cH:29][cH:30][cH:31][c:32]4[C:33]#[N:34])[cH:35][c:36]3[F:37])[c:38]2[s:39]1 | ([#7;a:4]:[c:5]:[n;H0;D3;+0:6](:[c:7])-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(O-B(-O)-[c;H0;D3;+0:1](:[c:2]):[c:3]).([#7;a:4]:[c:5]:[nH;D2;+0:6]:[c:7]) | b4d4c397aa388b9d90312475a7832eadf4dedc480cb1f9d75e80f51a | 1 | 1 | CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CCOC(C)=O.ClCCl.[Cu+2].c1ccncc1 | 962 |
120,201 | 446,186 | 758,220 | [CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[C:14]([C:28]4[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:27][CH2:26][CH2:25][CH2:24]5)[N:17]=4)=[C:9]3[CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>ClCCl>[CH:1]1([NH:6][C:7]2[CH:12]=[CH:11][N:10]3[N:13]=[C:14]([C:28]4[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=4)[C:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([NH:22][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[N:17]=4)=[C:9]3[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1 | null | US07141569B2_0680 | 2,006 | BrB(Br)Br.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[c:20]2-[c:21]2[cH:22][cH:23][n:24][c:25]([NH:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32]2)[cH:33][cH:34]1.ClCCl>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[c:20]2-[c:21]2[cH:22][cH:23][n:24][c:25]([NH:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32]2)[cH:33][cH:34]1 | 0.86952 | BrB(Br)Br.COc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(NC3CCCC3)n2)cc1.ClCCl>>Oc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(NC3CCCC3)n2)cc1 | BrB(Br)Br.COc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(NC3CCCC3)n2)cc1.ClCCl>>Oc1ccc(-c2nn3ccc(NC4CCCC4)cc3c2-c2ccnc(NC3CCCC3)n2)cc1 | US07141569B2_0680grants | e7894bd53a4ac84dbd263ae65210bfcf5df25a4f03dd199d9004ac7a | BrB(Br)Br.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[c:20]2-[c:21]2[cH:22][cH:23][n:24][c:25]([NH:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32]2)[cH:33][cH:34]1.ClCCl | [OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[n:7][n:8]3[cH:9][cH:10][c:11]([NH:12][CH:13]4[CH2:14][CH2:15][CH2:16][CH2:17]4)[cH:18][c:19]3[c:20]2-[c:21]2[cH:22][cH:23][n:24][c:25]([NH:26][CH:27]3[CH2:28][CH2:29][CH2:30][CH2:31]3)[n:32]2)[cH:33][cH:34]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCl | 48 |
102,175 | 391,477 | 669,151 | [Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[C@@H:11]1([NH2:21])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1>>[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:21][C@@H:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][CH2:12]1 | null | US06831193B2_ | 2,004 | O=[CH:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:20][c:18]1[Cl:19].[NH2:7][C@H:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21>>[Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C@H:8]2[CH2:9][CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[c:18]([Cl:19])[cH:20]1 | 0.989928 | N[C@H]1CCCc2ccccc21.O=Cc1ccc(Cl)cc1Cl>>Clc1ccc(CN[C@H]2CCCc3ccccc32)c(Cl)c1 | N[C@H]1CCCc2ccccc21.O=Cc1ccc(Cl)cc1Cl>>Clc1ccc(CN[C@H]2CCCc3ccccc32)c(Cl)c1 | US06831193B2_grants | 85fe6e1ec47ec6e12845ba44ba55f122d66c64ea77df157bcc01adf2 | O=[CH:6][c:5]1[cH:4][cH:3][c:2]([Cl:1])[cH:20][c:18]1[Cl:19].[NH2:7][C@H:8]1[CH2:9][CH2:10][CH2:11][c:12]2[cH:13][cH:14][cH:15][cH:16][c:17]21 | [Cl:1][c:2]1[cH:3][cH:4][c:5]([CH2:6][NH:7][C@H:8]2[CH2:9][CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[c:18]([Cl:19])[cH:20]1 | ([c:2]-[CH2;D2;+0:1]-[NH;D2;+0:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1)>>(O=[CH;D2;+0:1]-[c:2]).([NH2;D1;+0:3]-[C:4]-[c:5]1:[c:6]:[c:7]:[c:8]:[c:9]:[c:10]:1) | 24624f6f33a33ee7d79fdecddd4cc9b3195f73264de03dc892f32b12 | 1 | 1 | null | 683 |
323,009 | 1,049,863 | 1,781,656 | [H-].[Na+].[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4].F[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.O>CN(C=O)C>[N+:3]([C:6]1[C:14]2[N:13]=[CH:12][N:11]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1)([O-:5])=[O:4] | |f:0.1| | US09388140B2_0471 | 2,016 | CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:20][cH:19]1.O.[H-].[Na+].[nH:7]1[cH:8][n:9][c:10]2[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17][c:18]12>>[N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17][c:18]23)[cH:19][cH:20]1 | 0.953731 | CN(C)C=O.N#Cc1ccc(F)cc1.O.O=[N+]([O-])c1cccc2[nH]cnc12.[H-]~[Na+]>>N#Cc1ccc(-n2cnc3c([N+](=O)[O-])cccc32)cc1 | CN(C)C=O.N#Cc1ccc(F)cc1.O.O=[N+]([O-])c1cccc2[nH]cnc12.[H-].[Na+]>>N#Cc1ccc(-n2cnc3c([N+](=O)[O-])cccc32)cc1 | US09388140B2_0471grants | 41b97526add80991300631d6ac74e567545b810d8a09b6e6c5eb594c | CN(C)C=O.F[c:6]1[cH:5][cH:4][c:3]([C:2]#[N:1])[cH:20][cH:19]1.O.[H-].[Na+].[nH:7]1[cH:8][n:9][c:10]2[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17][c:18]12 | [N:1]#[C:2][c:3]1[cH:4][cH:5][c:6](-[n:7]2[cH:8][n:9][c:10]3[c:11]([N+:12](=[O:13])[O-:14])[cH:15][cH:16][cH:17][c:18]23)[cH:19][cH:20]1 | ([c:2]:[c;H0;D3;+0:1](:[c:3])-[n;H0;D3;+0:7]1:[c:6]:[c:5]:[#7;a:4]:[c:8]:1)>>(F-[c;H0;D3;+0:1](:[c:2]):[c:3]).([#7;a:4]1:[c:5]:[c:6]:[nH;D2;+0:7]:[c:8]:1) | eb3587f255eb4befff86cd7dc6cc1fbc3e76d628f2077d9856865993 | 1 | 1 | CN(C)C=O.O.[H-].[Na+] | 701 |
42,398 | 187,359 | 301,553 | [CH2:1]([C:5]1[NH:6][C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>O.C(O)(=O)C>[CH2:1]([C:5]1[NH:6][C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4] | |f:1.2| | US05350751_ | 1,994 | CC(=O)O.O.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH2:10][OH:11])[nH:12]1.[K+].[OH-]>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH:10]=[O:11])[nH:12]1 | 0.990661 | CC(=O)O.CCCCc1nc(Cl)c(CO)[nH]1.O.[K+]~[OH-]>>CCCCc1nc(Cl)c(C=O)[nH]1 | CC(=O)O.CCCCc1nc(Cl)c(CO)[nH]1.O.[K+].[OH-]>>CCCCc1nc(Cl)c(C=O)[nH]1 | US05350751_grants | 776744d3cbcdd15d252b86d9af7da44ef9f6c3bf99dd3bd99c22bfb4 | CC(=O)O.O.[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH2:10][OH:11])[nH:12]1.[K+].[OH-] | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]([Cl:8])[c:9]([CH:10]=[O:11])[nH:12]1 | ([#7;a:1]:[c:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4]):[c:5]:[#7;a:6])>>([#7;a:1]:[c:2](-[CH2;D2;+0:3]-[OH;D1;+0:4]):[c:5]:[#7;a:6]) | 1f2fbaaf61ae958e03167ccb7990c09c0994b1c6e4e7bd9ab5e14ae7 | 1 | 1 | CC(=O)O.O.[K+].[OH-] | 287 |
58,312 | 248,780 | 419,584 | CI.N12CCCN=C1CCCC[CH2:4]2.[CH2:14]([O:21][C:22]([CH2:24][C:25]1[C:38]2[S:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:46][CH3:47])[C:35]=3[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[N:30]([C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52]([OH:54])=[O:53])[C:29]=2[C:28]([CH2:56][NH2:57])=[CH:27][C:26]=1[O:58][CH3:59])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C)C=O.C(OCC)(=O)C>[CH2:14]([O:21][C:22]([CH2:24][C:25]1[C:38]2[S:37][C:36]3[C:31](=[CH:32][CH:33]=[C:34]([O:46][CH3:47])[C:35]=3[C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40])[N:30]([C:48](=[O:55])[CH2:49][CH2:50][CH2:51][C:52]([O:54][CH3:4])=[O:53])[C:29]=2[C:28]([CH2:56][NH2:57])=[CH:27][C:26]=1[O:58][CH3:59])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1 | null | US05811548_ | 1,998 | C1CCC2=NCCCN2CC1.CCOC(C)=O.CN(C)C=O.I[CH3:1].O.[OH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8](=[O:9])[N:10]1[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]2[S:26][c:27]2[c:28]([CH2:29][C:30](=[O:31])[O:32][CH2:33][c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]([O:41][CH3:42])[cH:43][c:44]([CH2:45][NH2:46])[c:47]21>>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8](=[O:9])[N:10]1[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]2[S:26][c:27]2[c:28]([CH2:29][C:30](=[O:31])[O:32][CH2:33][c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]([O:41][CH3:42])[cH:43][c:44]([CH2:45][NH2:46])[c:47]21 | 0.421917 | C1CCC2=NCCCN2CC1.CCOC(C)=O.CI.CN(C)C=O.COc1cc(CN)c2c(c1CC(=O)OCc1ccccc1)Sc1c(ccc(OC)c1C(=O)OC(C)(C)C)N2C(=O)CCCC(=O)O.O>>COC(=O)CCCC(=O)N1c2ccc(OC)c(C(=O)OC(C)(C)C)c2Sc2c(CC(=O)OCc3ccccc3)c(OC)cc(CN)c21 | C1CCC2=NCCCN2CC1.CCOC(C)=O.CI.CN(C)C=O.COc1cc(CN)c2c(c1CC(=O)OCc1ccccc1)Sc1c(ccc(OC)c1C(=O)OC(C)(C)C)N2C(=O)CCCC(=O)O.O>>COC(=O)CCCC(=O)N1c2ccc(OC)c(C(=O)OC(C)(C)C)c2Sc2c(CC(=O)OCc3ccccc3)c(OC)cc(CN)c21 | US05811548_grants | dba50befdff4ae9679d0b8e7117b18003d2f4493f89acbe1871b2dc8 | C1CCC2=NCCCN2CC1.CCOC(C)=O.CN(C)C=O.I[CH3:1].O.[OH:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8](=[O:9])[N:10]1[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]2[S:26][c:27]2[c:28]([CH2:29][C:30](=[O:31])[O:32][CH2:33][c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]([O:41][CH3:42])[cH:43][c:44]([CH2:45][NH2:46])[c:47]21 | [CH3:1][O:2][C:3](=[O:4])[CH2:5][CH2:6][CH2:7][C:8](=[O:9])[N:10]1[c:11]2[cH:12][cH:13][c:14]([O:15][CH3:16])[c:17]([C:18](=[O:19])[O:20][C:21]([CH3:22])([CH3:23])[CH3:24])[c:25]2[S:26][c:27]2[c:28]([CH2:29][C:30](=[O:31])[O:32][CH2:33][c:34]3[cH:35][cH:36][cH:37][cH:38][cH:39]3)[c:40]([O:41][CH3:42])[cH:43][c:44]([CH2:45][NH2:46])[c:47]21 | ([CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3]=[O;D1;H0:2])>>(I-[CH3;D1;+0:1]).([O;D1;H0:2]=[C:3]-[OH;D1;+0:4]) | c91e9563765e4a2f601b40326fcc9cfad1b5d00e212254922455906b | 1 | 1 | C1CCC2=NCCCN2CC1.CCOC(C)=O.CN(C)C=O.O | 415 |
188,719 | 650,979 | 1,075,996 | [CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=2)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>C(O)C.[Pd]>[CH:1]1([O:6][C:7](=[O:33])[C@@H:8]([N:15]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=2)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1 | null | US07939666B2_0707 | 2,011 | CCO.O=[N+:15]([O-])[c:14]1[cH:13][cH:12][cH:11][c:10]([CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:17]([C:18](=[O:19])[O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:16]1.[Pd]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]1)[C@H:17]([C:18](=[O:19])[O:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1 | 0.455504 | CC(C)(C)OC(=O)N(Cc1cccc([N+](=O)[O-])c1)[C@H](C(=O)OC1CCCC1)c1ccccc1.CCO.[Pd]>>CC(C)(C)OC(=O)N(Cc1cccc(N)c1)[C@H](C(=O)OC1CCCC1)c1ccccc1 | CC(C)(C)OC(=O)N(Cc1cccc([N+](=O)[O-])c1)[C@H](C(=O)OC1CCCC1)c1ccccc1.CCO.[Pd]>>CC(C)(C)OC(=O)N(Cc1cccc(N)c1)[C@H](C(=O)OC1CCCC1)c1ccccc1 | US07939666B2_0707grants | 3dfa2e96505251fcd9dd0c15a5166a1f1f16f9fe4924ebcfc2223866 | CCO.O=[N+:15]([O-])[c:14]1[cH:13][cH:12][cH:11][c:10]([CH2:9][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[C@H:17]([C:18](=[O:19])[O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[c:26]2[cH:27][cH:28][cH:29][cH:30][cH:31]2)[cH:16]1.[Pd] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]([CH2:9][c:10]1[cH:11][cH:12][cH:13][c:14]([NH2:15])[cH:16]1)[C@H:17]([C:18](=[O:19])[O:20][CH:21]1[CH2:22][CH2:23][CH2:24][CH2:25]1)[c:26]1[cH:27][cH:28][cH:29][cH:30][cH:31]1 | ([#7:8]-[C:7]-[c:6]1:[c:5]:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C:7]-[#7:8]):[c:9]:1) | 8ae831c82dc079dbdfba5f54795c649cace852fd2bea6506c3577b69 | 1 | 1 | CCO.[Pd] | 71 |
107,560 | 408,182 | 696,843 | [N:1]1([CH2:6][C@@H:7]([O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:21](=[O:25])[CH2:20][CH2:19][CH2:18][C:17]=3[C:16]=2[CH2:26][S:27]([C:30]2[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=2)[C:33](O)=[O:34])(=[O:29])=[O:28])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[NH2:39][CH:40]([CH2:43][OH:44])[CH2:41][OH:42]>>[OH:42][CH2:41][CH:40]([NH:39][C:33](=[O:34])[C:32]1[CH:36]=[CH:37][CH:38]=[C:30]([S:27]([CH2:26][C:16]2[C:17]3[CH2:18][CH2:19][CH2:20][C:21](=[O:25])[C:22]=3[CH:23]=[CH:24][C:15]=2[O:14][C@@H:7]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)(=[O:29])=[O:28])[CH:31]=1)[CH2:43][OH:44] | null | US06943183B2_1232 | 2,005 | O[C:2](=[O:1])[c:9]1[cH:10][cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:16])[CH2:17][c:18]2[c:19]([O:20][C@H:21]([CH2:22][n:23]3[cH:24][cH:25][n:26][cH:27]3)[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][cH:35][c:36]3[c:37]2[CH2:38][CH2:39][CH2:40][C:41]3=[O:42])[cH:43]1.[NH2:3][CH:4]([CH2:5][OH:6])[CH2:7][OH:8]>>[O:1]=[C:2]([NH:3][CH:4]([CH2:5][OH:6])[CH2:7][OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:16])[CH2:17][c:18]2[c:19]([O:20][C@H:21]([CH2:22][n:23]3[cH:24][cH:25][n:26][cH:27]3)[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][cH:35][c:36]3[c:37]2[CH2:38][CH2:39][CH2:40][C:41]3=[O:42])[cH:43]1 | 0.467658 | NC(CO)CO.O=C(O)c1cccc(S(=O)(=O)Cc2c(O[C@H](Cn3ccnc3)c3ccccc3)ccc3c2CCCC3=O)c1>>O=C(NC(CO)CO)c1cccc(S(=O)(=O)Cc2c(O[C@H](Cn3ccnc3)c3ccccc3)ccc3c2CCCC3=O)c1 | NC(CO)CO.O=C(O)c1cccc(S(=O)(=O)Cc2c(O[C@H](Cn3ccnc3)c3ccccc3)ccc3c2CCCC3=O)c1>>O=C(NC(CO)CO)c1cccc(S(=O)(=O)Cc2c(O[C@H](Cn3ccnc3)c3ccccc3)ccc3c2CCCC3=O)c1 | US06943183B2_1232grants | 185d90922dcd0735fdd2aeccc63f653728a753af3ecf294d5a19a405 | O[C:2](=[O:1])[c:9]1[cH:10][cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:16])[CH2:17][c:18]2[c:19]([O:20][C@H:21]([CH2:22][n:23]3[cH:24][cH:25][n:26][cH:27]3)[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][cH:35][c:36]3[c:37]2[CH2:38][CH2:39][CH2:40][C:41]3=[O:42])[cH:43]1.[NH2:3][CH:4]([CH2:5][OH:6])[CH2:7][OH:8] | [O:1]=[C:2]([NH:3][CH:4]([CH2:5][OH:6])[CH2:7][OH:8])[c:9]1[cH:10][cH:11][cH:12][c:13]([S:14](=[O:15])(=[O:16])[CH2:17][c:18]2[c:19]([O:20][C@H:21]([CH2:22][n:23]3[cH:24][cH:25][n:26][cH:27]3)[c:28]3[cH:29][cH:30][cH:31][cH:32][cH:33]3)[cH:34][cH:35][c:36]3[c:37]2[CH2:38][CH2:39][CH2:40][C:41]3=[O:42])[cH:43]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | null | 334 |
334,495 | 192,376 | null | [Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[CH:15][N:14]=3)=[CH:9][CH:8]=2)=[C:4]([F:24])[CH:3]=1.C(C1NC=CN=1)(C1[NH:28]C=CN=1)=O.C([O-])(=O)C.[NH4+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]([C:19]([NH2:28])=[O:20])[CH:16]=[CH:15][N:14]=3)=[CH:11][CH:12]=2)=[C:4]([F:24])[CH:3]=1 | |f:2.3| | US20040192691A1_0286 | 2,004 | CC(=O)[O-].CCOC(C)=O.CN(C)C=O.O=C(c1ncc[nH]1)c1ncc[nH]1.O[C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[F:21])[cH:22][cH:23]2)[n:24]1.[NH4+:1]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[F:21])[cH:22][cH:23]2)[n:24]1 | 0.63891 | CC(=O)[O-]~[NH4+].CCOC(C)=O.CN(C)C=O.O=C(O)c1ccnc(-c2ccc(Oc3ccc(Cl)cc3F)cc2)n1.O=C(c1ncc[nH]1)c1ncc[nH]1>>NC(=O)c1ccnc(-c2ccc(Oc3ccc(Cl)cc3F)cc2)n1 | CC(=O)[O-].CCOC(C)=O.CN(C)C=O.O=C(O)c1ccnc(-c2ccc(Oc3ccc(Cl)cc3F)cc2)n1.O=C(c1ncc[nH]1)c1ncc[nH]1.[NH4+]>>NC(=O)c1ccnc(-c2ccc(Oc3ccc(Cl)cc3F)cc2)n1 | US20040192691A1_0286apps | eede1fba4b4c4d1e90cd932ab9edafccb3195266000ad98f01a20bb4 | CC(=O)[O-].CCOC(C)=O.CN(C)C=O.O=C(c1ncc[nH]1)c1ncc[nH]1.O[C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[F:21])[cH:22][cH:23]2)[n:24]1.[NH4+:1] | [NH2:1][C:2](=[O:3])[c:4]1[cH:5][cH:6][n:7][c:8](-[c:9]2[cH:10][cH:11][c:12]([O:13][c:14]3[cH:15][cH:16][c:17]([Cl:18])[cH:19][c:20]3[F:21])[cH:22][cH:23]2)[n:24]1 | ([#7;a:4]:[c:3]-[C;H0;D3;+0:1](-[NH2;D1;+0:5])=[O;D1;H0:2])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]).([NH4+;D0:5]) | 993f6da7daa9e50278764df7b42b26298b276c8161ca892bef8c8386 | 1 | 1 | CC(=O)[O-].CCOC(C)=O.CN(C)C=O.O=C(c1ncc[nH]1)c1ncc[nH]1 | 136 |
66,045 | 276,198 | 468,725 | N1C=CC=CC=1.[C:7](OC(=O)C)(=[O:9])[CH3:8].CN(C1C=CC=CN=1)C.[C:23]([N:33]1[CH2:36][CH:35]([C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH2:47][C@H:46]([CH2:48][NH2:49])[O:45][C:44]3=[O:50])=[CH:39][C:38]=2[F:51])[CH2:34]1)([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>C(Cl)Cl>[F:51][C:38]1[CH:39]=[C:40]([N:43]2[CH2:47][C@H:46]([CH2:48][NH:49][C:7](=[O:9])[CH3:8])[O:45][C:44]2=[O:50])[CH:41]=[CH:42][C:37]=1[CH:35]1[CH2:36][N:33]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:34]1 | null | US06043266_ | 2,000 | CC(=O)O[C:2]([CH3:1])=[O:3].CN(C)c1ccccn1.ClCCl.[NH2:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[CH2:26]3)[c:27]([F:28])[cH:29]2)[C:30](=[O:31])[O:32]1.c1ccncc1>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[CH2:26]3)[c:27]([F:28])[cH:29]2)[C:30](=[O:31])[O:32]1 | 0.40727 | CC(=O)OC(C)=O.CN(C)c1ccccn1.ClCCl.NC[C@H]1CN(c2ccc(C3CN(C(=O)OCc4ccccc4)C3)c(F)c2)C(=O)O1.c1ccncc1>>CC(=O)NC[C@H]1CN(c2ccc(C3CN(C(=O)OCc4ccccc4)C3)c(F)c2)C(=O)O1 | CC(=O)OC(C)=O.CN(C)c1ccccn1.ClCCl.NC[C@H]1CN(c2ccc(C3CN(C(=O)OCc4ccccc4)C3)c(F)c2)C(=O)O1.c1ccncc1>>CC(=O)NC[C@H]1CN(c2ccc(C3CN(C(=O)OCc4ccccc4)C3)c(F)c2)C(=O)O1 | US06043266_grants | f4d9b353dc29fa6ef13f656dd69022f87e167ed1318c91c11bd7fc3e | CC(=O)O[C:2]([CH3:1])=[O:3].CN(C)c1ccccn1.ClCCl.[NH2:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[CH2:26]3)[c:27]([F:28])[cH:29]2)[C:30](=[O:31])[O:32]1.c1ccncc1 | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([CH:13]3[CH2:14][N:15]([C:16](=[O:17])[O:18][CH2:19][c:20]4[cH:21][cH:22][cH:23][cH:24][cH:25]4)[CH2:26]3)[c:27]([F:28])[cH:29]2)[C:30](=[O:31])[O:32]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3])>>(C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 485f1a5fe8e94fe10384157e43b0e7c377df1c902531cf76de6081c3 | 1 | 1 | CN(C)c1ccccn1.ClCCl.c1ccncc1 | 339 |
315,712 | 1,026,188 | 1,737,655 | [CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[C:14]([O:18][CH2:19][CH2:20][C:21]([OH:23])=O)[C:15]([I:17])=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH2:11][C:10]2[C:13]3[C:21](=[O:23])[CH2:20][CH2:19][O:18][C:14]=3[C:15]([I:17])=[CH:16][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2] | |f:2.3.4.5| | US09284277B2_0380 | 2,016 | CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:18](=[O:19])[CH2:20][CH2:21][O:22][c:13]1[c:11]([I:12])[cH:10][c:9]2[c:15]([cH:14]1)[CH2:16][CH2:17][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8]2.[Al+3].[Cl-].[Cl-].[Cl-]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([I:12])[c:13]3[c:14]([c:15]2[CH2:16][CH2:17]1)[C:18](=[O:19])[CH2:20][CH2:21][O:22]3 | 0.823521 | CCOC(=O)N1CCc2cc(I)c(OCCC(=O)O)cc2CC1.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.[Al+3]~[Cl-]~[Cl-]~[Cl-]>>CCOC(=O)N1CCc2cc(I)c3c(c2CC1)C(=O)CCO3 | CCOC(=O)N1CCc2cc(I)c(OCCC(=O)O)cc2CC1.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.[Al+3].[Cl-].[Cl-].[Cl-]>>CCOC(=O)N1CCc2cc(I)c3c(c2CC1)C(=O)CCO3 | US09284277B2_0380grants | bca73ba413905ffb87156d806bc2a0bb6bb8c33e6b03c1caf84e8359 | CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:18](=[O:19])[CH2:20][CH2:21][O:22][c:13]1[c:11]([I:12])[cH:10][c:9]2[c:15]([cH:14]1)[CH2:16][CH2:17][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:7][CH2:8]2.[Al+3].[Cl-].[Cl-].[Cl-] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][c:9]2[cH:10][c:11]([I:12])[c:13]3[c:14]([c:15]2[CH2:16][CH2:17]1)[C:18](=[O:19])[CH2:20][CH2:21][O:22]3 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3].[c:4]:[cH;D2;+0:5]:[c:6]) | a7d77ace8169e6422b0d679b606a91f7d2decee976f91184f657dc85 | 0 | 1 | CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.[Al+3].[Cl-].[Cl-].[Cl-] | 274 |
369,262 | 749,035 | null | CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][CH:20]([OH:22])[CH2:19][N:18]([C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:17]1)=[O:15])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[CH2:11]([O:13][C:14]([CH:16]1[CH2:21][C:20](=[O:22])[CH2:19][N:18]([C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:17]1)=[O:15])[CH3:12] | null | US20090203737A1_0588 | 2,009 | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH:8]([OH:9])[CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][C:8](=[O:9])[CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21]1 | 0.942455 | CCN(CC)CC.CCOC(=O)C1CC(O)CN(C(=O)c2ccc(F)cc2)C1.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CCOC(=O)C1CC(=O)CN(C(=O)c2ccc(F)cc2)C1 | CCN(CC)CC.CCOC(=O)C1CC(O)CN(C(=O)c2ccc(F)cc2)C1.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl>>CCOC(=O)C1CC(=O)CN(C(=O)c2ccc(F)cc2)C1 | US20090203737A1_0588apps | 5360bf1f6f89f400ce06db23e9f7d47d4c7f303717ba151883051382 | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH:8]([OH:9])[CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][C:8](=[O:9])[CH2:10][N:11]([C:12](=[O:13])[c:14]2[cH:15][cH:16][c:17]([F:18])[cH:19][cH:20]2)[CH2:21]1 | ([#7:1]-[C:2]-[C;H0;D3;+0:3](-[C:4])=[O;H0;D1;+0:5])>>([#7:1]-[C:2]-[CH;D3;+0:3](-[C:4])-[OH;D1;+0:5]) | 8648225a22348f7e6baafae96bc82cc877edf2fed51c1efd5b40ee8e | 1 | 1 | CCN(CC)CC.CS(C)=O.ClCCl.O=C(Cl)C(=O)Cl | 650 |
175,126 | 611,636 | 1,013,907 | [N:1]1([NH:7][C:8]([C:10]2[N:11]=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[C:14]=2[CH3:15])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[F:38][C:39]([F:47])([F:46])[CH2:40][CH2:41][S:42](Cl)(=[O:44])=[O:43].O>ClCCl>[Cl:30][C:24]1[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:23]=1[C:12]1[N:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][S:42]([CH2:41][CH2:40][C:39]([F:47])([F:46])[F:38])(=[O:44])=[O:43])=[CH:20][CH:21]=2)[C:14]([CH3:15])=[C:10]([C:8](=[O:9])[NH:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:11]=1 | null | US07799804B2_0301 | 2,010 | CCN(CC)CC.ClCCl.Cl[S:29](=[O:30])(=[O:31])[CH2:32][CH2:33][C:34]([F:35])([F:36])[F:37].O.[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[Cl:22])[n:23]1-[c:24]1[cH:25][cH:26][c:27]([OH:28])[cH:38][cH:39]1>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[Cl:22])[n:23]1-[c:24]1[cH:25][cH:26][c:27]([O:28][S:29](=[O:30])(=[O:31])[CH2:32][CH2:33][C:34]([F:35])([F:36])[F:37])[cH:38][cH:39]1 | 0.184028 | CCN(CC)CC.Cc1c(C(=O)NN2CCCCC2)nc(-c2ccc(Cl)cc2Cl)n1-c1ccc(O)cc1.ClCCl.O.O=S(=O)(Cl)CCC(F)(F)F>>Cc1c(C(=O)NN2CCCCC2)nc(-c2ccc(Cl)cc2Cl)n1-c1ccc(OS(=O)(=O)CCC(F)(F)F)cc1 | CCN(CC)CC.Cc1c(C(=O)NN2CCCCC2)nc(-c2ccc(Cl)cc2Cl)n1-c1ccc(O)cc1.ClCCl.O.O=S(=O)(Cl)CCC(F)(F)F>>Cc1c(C(=O)NN2CCCCC2)nc(-c2ccc(Cl)cc2Cl)n1-c1ccc(OS(=O)(=O)CCC(F)(F)F)cc1 | US07799804B2_0301grants | 7453f6cf2e7ac0b065ed4ef4efb52d66eeee4a409aedcbb4a905ad76 | CCN(CC)CC.ClCCl.Cl[S:29](=[O:30])(=[O:31])[CH2:32][CH2:33][C:34]([F:35])([F:36])[F:37].O.[CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[Cl:22])[n:23]1-[c:24]1[cH:25][cH:26][c:27]([OH:28])[cH:38][cH:39]1 | [CH3:1][c:2]1[c:3]([C:4](=[O:5])[NH:6][N:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[n:13][c:14](-[c:15]2[cH:16][cH:17][c:18]([Cl:19])[cH:20][c:21]2[Cl:22])[n:23]1-[c:24]1[cH:25][cH:26][c:27]([O:28][S:29](=[O:30])(=[O:31])[CH2:32][CH2:33][C:34]([F:35])([F:36])[F:37])[cH:38][cH:39]1 | ([C:2]-[S;H0;D4;+0:1](=[O;D1;H0:3])(=[O;D1;H0:4])-[O;H0;D2;+0:5]-[c:6])>>(Cl-[S;H0;D4;+0:1](-[C:2])(=[O;D1;H0:3])=[O;D1;H0:4]).([OH;D1;+0:5]-[c:6]) | 67582b0d0547b3e93f28b377d38428ed5ddd35bc8efb5326096b9ab7 | 1 | 1 | CCN(CC)CC.ClCCl.O | 149 |
229,483 | 767,901 | 1,266,277 | [N:1]([CH2:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][B:10]([OH:18])[C:9]=2[CH:8]=[C:7]([O:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:6]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[C:13]2[CH:12]([CH2:14][C:15]([OH:17])=[O:16])[O:11][B:10]([OH:18])[C:9]=2[CH:8]=[C:7]([O:19][C:20]2[CH:25]=[N:24][CH:23]=[CH:22][N:21]=2)[CH:6]=1 | |f:2.3| | US08343944B2_1089 | 2,013 | C1CCOC1.O.[N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[cH:13][c:14]2[c:15]1[CH:16]([CH2:17][C:18](=[O:19])[OH:20])[O:21][B:22]2[OH:23].c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[NH2:1][CH2:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[cH:13][c:14]2[c:15]1[CH:16]([CH2:17][C:18](=[O:19])[OH:20])[O:21][B:22]2[OH:23] | 0.959597 | C1CCOC1~O.[N-]=[N+]=NCc1cc(Oc2cnccn2)cc2c1C(CC(=O)O)OB2O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>NCc1cc(Oc2cnccn2)cc2c1C(CC(=O)O)OB2O | C1CCOC1.O.[N-]=[N+]=NCc1cc(Oc2cnccn2)cc2c1C(CC(=O)O)OB2O.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>NCc1cc(Oc2cnccn2)cc2c1C(CC(=O)O)OB2O | US08343944B2_1089grants | a8ee361b18ec4106c549422d236716a37192434266a36336f261d32e | C1CCOC1.O.[N-]=[N+]=[N:1][CH2:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[cH:13][c:14]2[c:15]1[CH:16]([CH2:17][C:18](=[O:19])[OH:20])[O:21][B:22]2[OH:23].c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [NH2:1][CH2:2][c:3]1[cH:4][c:5]([O:6][c:7]2[cH:8][n:9][cH:10][cH:11][n:12]2)[cH:13][c:14]2[c:15]1[CH:16]([CH2:17][C:18](=[O:19])[OH:20])[O:21][B:22]2[OH:23] | ([NH2;D1;+0:1]-[C:2]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1)>>([N-]=[N+]=[N;H0;D2;+0:1]-[C:2]-[c:3]1:[c:4]:[c:5]:[c:6]:[c:7]:[c:8]:1) | 40249e68358278d504131b6575e42710f2a18bfde5b872029b431d5d | 1 | 1 | C1CCOC1.O.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 562 |
188,779 | 651,139 | 1,076,299 | C[O:2][C:3](=[O:36])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]#[C:15][C:16]2[CH:21]=[C:20]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)[CH:19]=[C:18]([Br:34])[CH:17]=2)=[CH:8][C:7]=1[CH3:35]>C(O)C.[OH-].[Na+]>[Br:34][C:18]1[CH:17]=[C:16]([C:15]#[C:14][CH2:13][O:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:4][C:3]([OH:36])=[O:2])=[C:7]([CH3:35])[CH:8]=2)[CH:21]=[C:20]([C:22]#[C:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:33])[F:31])=[CH:26][CH:25]=2)[CH:19]=1 | |f:2.3| | US07943612B2_0465 | 2,011 | CCO.C[O:35][C:33]([CH2:32][O:31][c:30]1[c:2]([CH3:1])[cH:3][c:4]([O:5][CH2:6][C:7]#[C:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]3)[cH:27]2)[cH:28][cH:29]1)=[O:34].[Na+].[OH-]>>[CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]#[C:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]3)[cH:27]2)[cH:28][cH:29][c:30]1[O:31][CH2:32][C:33](=[O:34])[OH:35] | 0.2413 | CCO.COC(=O)COc1ccc(OCC#Cc2cc(Br)cc(C#Cc3ccc(C(F)(F)F)cc3)c2)cc1C.[Na+]~[OH-]>>Cc1cc(OCC#Cc2cc(Br)cc(C#Cc3ccc(C(F)(F)F)cc3)c2)ccc1OCC(=O)O | CCO.COC(=O)COc1ccc(OCC#Cc2cc(Br)cc(C#Cc3ccc(C(F)(F)F)cc3)c2)cc1C.[Na+].[OH-]>>Cc1cc(OCC#Cc2cc(Br)cc(C#Cc3ccc(C(F)(F)F)cc3)c2)ccc1OCC(=O)O | US07943612B2_0465grants | b8de0dc340b8b77695f9f8bf1b333e6893e708f3b5edd06ecf0bb7f2 | CCO.C[O:35][C:33]([CH2:32][O:31][c:30]1[c:2]([CH3:1])[cH:3][c:4]([O:5][CH2:6][C:7]#[C:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]3)[cH:27]2)[cH:28][cH:29]1)=[O:34].[Na+].[OH-] | [CH3:1][c:2]1[cH:3][c:4]([O:5][CH2:6][C:7]#[C:8][c:9]2[cH:10][c:11]([Br:12])[cH:13][c:14]([C:15]#[C:16][c:17]3[cH:18][cH:19][c:20]([C:21]([F:22])([F:23])[F:24])[cH:25][cH:26]3)[cH:27]2)[cH:28][cH:29][c:30]1[O:31][CH2:32][C:33](=[O:34])[OH:35] | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CCO.[Na+].[OH-] | 88 |
391,100 | 1,168,987 | null | C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([SH:23])=[CH:19][CH:18]=1.O>C(#N)C.C(OCC)(=O)C>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][S:23][C:20]1[CH:21]=[CH:22][C:17]([CH3:16])=[CH:18][CH:19]=1)[CH3:15] | |f:0.1.2| | US20120022054A1_0948 | 2,012 | Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CC#N.CCOC(C)=O.O.O=C([O-])[O-].[K+].[K+].[SH:9][c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | 0.897178 | CC#N.CCOC(=O)CCCBr.CCOC(C)=O.Cc1ccc(S)cc1.O.O=C([O-])[O-]~[K+]~[K+]>>CCOC(=O)CCCSc1ccc(C)cc1 | CC#N.CCOC(=O)CCCBr.CCOC(C)=O.Cc1ccc(S)cc1.O.O=C([O-])[O-].[K+].[K+]>>CCOC(=O)CCCSc1ccc(C)cc1 | US20120022054A1_0948apps | 8ae389f66e3e17101fd3735f3a53c0cc91d126901d374ef42016234f | Br[CH2:8][CH2:7][CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5].CC#N.CCOC(C)=O.O.O=C([O-])[O-].[K+].[K+].[SH:9][c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH2:7][CH2:8][S:9][c:10]1[cH:11][cH:12][c:13]([CH3:14])[cH:15][cH:16]1 | ([C:2]-[CH2;D2;+0:1]-[S;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([SH;D1;+0:3]-[c:4]) | b73d38e46252a190f18366e71c7fd160a59a139df9fb6551d999a041 | 1 | 1 | CC#N.CCOC(C)=O.O.O=C([O-])[O-].[K+].[K+] | 124 |
218,686 | 735,034 | 1,211,165 | [CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=2.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C=O)C>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:18]([C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:9]([C:3]4[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[NH:10]3)=[CH:15][CH:14]=2)=[O:19])=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23] | |f:2.3| | US08222248B2_1241 | 2,012 | CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:15]([c:14]1[cH:13][cH:12][c:11]2[cH:10][c:9](-[c:8]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]3[CH3:7])[nH:30][c:29]2[cH:28]1)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1-[c:9]1[cH:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]3[cH:19][cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]3)[cH:28][c:29]2[nH:30]1 | 0.374853 | CC(C)(C)c1ccc(N)cc1.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.Cc1cccc(C)c1-c1cc2ccc(C(=O)O)cc2[nH]1>>Cc1cccc(C)c1-c1cc2ccc(C(=O)Nc3ccc(C(C)(C)C)cc3)cc2[nH]1 | CC(C)(C)c1ccc(N)cc1.CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.Cc1cccc(C)c1-c1cc2ccc(C(=O)O)cc2[nH]1.F[P-](F)(F)(F)(F)F>>Cc1cccc(C)c1-c1cc2ccc(C(=O)Nc3ccc(C(C)(C)C)cc3)cc2[nH]1 | US08222248B2_1241grants | c5bed2736b07fe001cae97801d8c9e31447aea35a9ef563168bae6a6 | CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F.O[C:15]([c:14]1[cH:13][cH:12][c:11]2[cH:10][c:9](-[c:8]3[c:2]([CH3:1])[cH:3][cH:4][cH:5][c:6]3[CH3:7])[nH:30][c:29]2[cH:28]1)=[O:16].[NH2:17][c:18]1[cH:19][cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]1 | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH3:7])[c:8]1-[c:9]1[cH:10][c:11]2[cH:12][cH:13][c:14]([C:15](=[O:16])[NH:17][c:18]3[cH:19][cH:20][c:21]([C:22]([CH3:23])([CH3:24])[CH3:25])[cH:26][cH:27]3)[cH:28][c:29]2[nH:30]1 | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 35b8cb0d38b7801143c15d7c216f0b66c154f00ac243d1252d6d0e55 | 1 | 1 | CCOC(C)=O.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.F[P-](F)(F)(F)(F)F | 50 |
186,300 | 643,963 | 1,064,681 | C[O:2][C:3](=O)[CH2:4][NH:5][C:6](=[S:10])[CH2:7][CH2:8][CH3:9].[NH3:12]>CO>[C:6]([NH:5][CH2:4][C:3]([NH2:12])=[O:2])(=[S:10])[CH2:7][CH2:8][CH3:9] | null | US07915411B2_0461 | 2,011 | CO.CO[C:8]([CH2:7][NH:6][C:4]([CH2:3][CH2:2][CH3:1])=[S:5])=[O:10].[NH3:9]>>[CH3:1][CH2:2][CH2:3][C:4](=[S:5])[NH:6][CH2:7][C:8]([NH2:9])=[O:10] | 0.9418 | CCCC(=S)NCC(=O)OC.CO.N>>CCCC(=S)NCC(N)=O | CCCC(=S)NCC(=O)OC.CO.N>>CCCC(=S)NCC(N)=O | US07915411B2_0461grants | 0de976d4358590d34d2607337c1b3a06ae115438af23b92030dd21d6 | CO.CO[C:8]([CH2:7][NH:6][C:4]([CH2:3][CH2:2][CH3:1])=[S:5])=[O:10].[NH3:9] | [CH3:1][CH2:2][CH2:3][C:4](=[S:5])[NH:6][CH2:7][C:8]([NH2:9])=[O:10] | ([C:2]-[C;H0;D3;+0:1](-[NH2;D1;+0:4])=[O;D1;H0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH3;D0;+0:4]) | 32b2d076d42f6c5d0d9e42aaee8ea11f9f6bde1dfbde54d0a3f692c3 | 1 | 1 | CO | 432 |
164,806 | 580,342 | 965,474 | [O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][C:3]1([CH3:27])[CH3:26].[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH2:18][C@H:17]([CH2:19][NH:20][C:21](=[O:23])[CH3:22])[O:16][C:15]3=[O:24])=[CH:10][C:9]=2[F:25])[CH2:4][C:3]1([CH3:27])[CH3:26] | |f:1.2| | US07687627B2_1240 | 2,010 | CO.[BH4-].[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[CH2:21]3)[c:22]([F:23])[cH:24]2)[C:25](=[O:26])[O:27]1.[Na+]>>[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([OH:17])[C:18]([CH3:19])([CH3:20])[CH2:21]3)[c:22]([F:23])[cH:24]2)[C:25](=[O:26])[O:27]1 | 0.671121 | CC(=O)NC[C@H]1CN(c2ccc(N3CCC(=O)C(C)(C)C3)c(F)c2)C(=O)O1.CO.[BH4-]~[Na+]>>CC(=O)NC[C@H]1CN(c2ccc(N3CCC(O)C(C)(C)C3)c(F)c2)C(=O)O1 | CC(=O)NC[C@H]1CN(c2ccc(N3CCC(=O)C(C)(C)C3)c(F)c2)C(=O)O1.CO.[BH4-].[Na+]>>CC(=O)NC[C@H]1CN(c2ccc(N3CCC(O)C(C)(C)C3)c(F)c2)C(=O)O1 | US07687627B2_1240grants | 241a56ad2681e046ae96d45d5970975ce31acc72ac82e20fa66994f5 | CO.[BH4-].[CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][C:16](=[O:17])[C:18]([CH3:19])([CH3:20])[CH2:21]3)[c:22]([F:23])[cH:24]2)[C:25](=[O:26])[O:27]1.[Na+] | [CH3:1][C:2](=[O:3])[NH:4][CH2:5][C@H:6]1[CH2:7][N:8]([c:9]2[cH:10][cH:11][c:12]([N:13]3[CH2:14][CH2:15][CH:16]([OH:17])[C:18]([CH3:19])([CH3:20])[CH2:21]3)[c:22]([F:23])[cH:24]2)[C:25](=[O:26])[O:27]1 | ([C:1]-[CH;D3;+0:2](-[C:3])-[OH;D1;+0:4])>>([C:1]-[C;H0;D3;+0:2](-[C:3])=[O;H0;D1;+0:4]) | 0fb396942a5bc824558e6936c3618c2e342b489a89eccebed032da69 | 1 | 1 | CO.[BH4-].[Na+] | 91 |
411,588 | 1,656,853 | null | Br[C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[CH:12]=[CH:11][N:10]=2)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[C:18]([C@:20]1([OH:27])[CH2:24][CH2:23][N:22]([CH3:25])[C:21]1=[O:26])#[CH:19]>>[OH:27][C@@:20]1([C:18]#[C:19][C:2]2[CH:3]=[C:4]([C:9]3[N:14]=[C:13]([C:15]([NH2:17])=[O:16])[CH:12]=[CH:11][N:10]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=2)[CH2:24][CH2:23][N:22]([CH3:25])[C:21]1=[O:26] | null | US20150057260A1_0932 | 2,015 | Br[c:4]1[cH:3][c:2]([CH3:1])[cH:26][c:16](-[c:17]2[n:18][cH:19][cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25]2)[cH:15]1.[CH:5]#[C:6][C@:7]1([OH:8])[CH2:9][CH2:10][N:11]([CH3:12])[C:13]1=[O:14]>>[CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][C@:7]2([OH:8])[CH2:9][CH2:10][N:11]([CH3:12])[C:13]2=[O:14])[cH:15][c:16](-[c:17]2[n:18][cH:19][cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25]2)[cH:26]1 | 0.964021 | C#C[C@]1(O)CCN(C)C1=O.Cc1cc(Br)cc(-c2nccc(C(N)=O)n2)c1>>Cc1cc(C#C[C@]2(O)CCN(C)C2=O)cc(-c2nccc(C(N)=O)n2)c1 | C#C[C@]1(O)CCN(C)C1=O.Cc1cc(Br)cc(-c2nccc(C(N)=O)n2)c1>>Cc1cc(C#C[C@]2(O)CCN(C)C2=O)cc(-c2nccc(C(N)=O)n2)c1 | US20150057260A1_0932apps | 2a821c7f0e07bfe844b1aef06824e25597f7e09d965a6414df99fde6 | Br[c:4]1[cH:3][c:2]([CH3:1])[cH:26][c:16](-[c:17]2[n:18][cH:19][cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25]2)[cH:15]1.[CH:5]#[C:6][C@:7]1([OH:8])[CH2:9][CH2:10][N:11]([CH3:12])[C:13]1=[O:14] | [CH3:1][c:2]1[cH:3][c:4]([C:5]#[C:6][C@:7]2([OH:8])[CH2:9][CH2:10][N:11]([CH3:12])[C:13]2=[O:14])[cH:15][c:16](-[c:17]2[n:18][cH:19][cH:20][c:21]([C:22]([NH2:23])=[O:24])[n:25]2)[cH:26]1 | ([C:4]#[C;H0;D2;+0:5]-[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]#[CH;D1;+0:5]) | 42f697fc7ae70923f5806984441d2582468344af75caeb7e213f1b10 | 1 | 1 | null | 659 |
260,460 | 860,137 | 1,430,434 | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:13]3[CH2:15][CH2:14]3)[NH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:16](=O)([O-])[O-].[Cs+].[Cs+].IC.O>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:13]3[CH2:15][CH2:14]3)[N:11]([CH3:16])[CH:12]=2)=[CH:6][CH:7]=1 | |f:1.2.3| | US08664253B2_0437 | 2,014 | C1CCOC1.I[CH3:1].O.O=C([O-])[O-].[Cs+].[Cs+].[nH:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[n:12][c:13]1[CH:14]1[CH2:15][CH2:16]1>>[CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[n:12][c:13]1[CH:14]1[CH2:15][CH2:16]1 | 0.865714 | Brc1ccc(-c2c[nH]c(C3CC3)n2)cc1.C1CCOC1.CI.O.O=C([O-])[O-]~[Cs+]~[Cs+]>>Cn1cc(-c2ccc(Br)cc2)nc1C1CC1 | Brc1ccc(-c2c[nH]c(C3CC3)n2)cc1.C1CCOC1.CI.O.O=C([O-])[O-].[Cs+].[Cs+]>>Cn1cc(-c2ccc(Br)cc2)nc1C1CC1 | US08664253B2_0437grants | 6ee0780fe0ceb6e359d71ddc9e2c86abfa879b50283923d11b1e5467 | C1CCOC1.I[CH3:1].O.O=C([O-])[O-].[Cs+].[Cs+].[nH:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[n:12][c:13]1[CH:14]1[CH2:15][CH2:16]1 | [CH3:1][n:2]1[cH:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]2)[n:12][c:13]1[CH:14]1[CH2:15][CH2:16]1 | ([CH3;D1;+0:1]-[n;H0;D3;+0:4]1:[c:3]:[#7;a:2]:[c:6]:[c:5]:1)>>(I-[CH3;D1;+0:1]).([#7;a:2]1:[c:3]:[nH;D2;+0:4]:[c:5]:[c:6]:1) | 207930f1d045bf906edec9c38d46a6e9d2f1d1d1d087bd483a3dd083 | 1 | 1 | C1CCOC1.O.O=C([O-])[O-].[Cs+].[Cs+] | 404 |
168,602 | 592,014 | 982,160 | [NH2:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=23)=[C:4]([F:20])[CH:3]=1.Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([NH2:28])[N:23]=1.Cl.[OH-].[Na+]>O.CO.C(O)C>[NH2:28][C:24]1[N:25]=[C:26]([NH:1][C:2]2[CH:19]=[CH:18][C:5]([CH2:6][C:7]3[CH:12]=[CH:11][N:10]=[C:9]4[NH:13][CH:14]=[C:15]([C:16]#[N:17])[C:8]=34)=[C:4]([F:20])[CH:3]=2)[CH:27]=[CH:22][N:23]=1 | |f:3.4| | US07723347B2_0747 | 2,010 | CCO.CO.Cl.Cl[c:17]1[cH:18][cH:19][n:20][c:21]([NH2:22])[n:23]1.O.[N:1]#[C:2][c:3]1[cH:4][nH:5][c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][c:12]3[cH:13][cH:14][c:15]([NH2:16])[cH:24][c:25]3[F:26])[c:27]12.[Na+].[OH-]>>[N:1]#[C:2][c:3]1[cH:4][nH:5][c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][c:12]3[cH:13][cH:14][c:15]([NH:16][c:17]4[cH:18][cH:19][n:20][c:21]([NH2:22])[n:23]4)[cH:24][c:25]3[F:26])[c:27]12 | 0.989856 | CCO.CO.Cl.N#Cc1c[nH]c2nccc(Cc3ccc(N)cc3F)c12.Nc1nccc(Cl)n1.O.[Na+]~[OH-]>>N#Cc1c[nH]c2nccc(Cc3ccc(Nc4ccnc(N)n4)cc3F)c12 | CCO.CO.Cl.N#Cc1c[nH]c2nccc(Cc3ccc(N)cc3F)c12.Nc1nccc(Cl)n1.O.[Na+].[OH-]>>N#Cc1c[nH]c2nccc(Cc3ccc(Nc4ccnc(N)n4)cc3F)c12 | US07723347B2_0747grants | 9b605534eadbc63fa8e9b48a667e5a220c618fbe4283ec455b21c997 | CCO.CO.Cl.Cl[c:17]1[cH:18][cH:19][n:20][c:21]([NH2:22])[n:23]1.O.[N:1]#[C:2][c:3]1[cH:4][nH:5][c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][c:12]3[cH:13][cH:14][c:15]([NH2:16])[cH:24][c:25]3[F:26])[c:27]12.[Na+].[OH-] | [N:1]#[C:2][c:3]1[cH:4][nH:5][c:6]2[n:7][cH:8][cH:9][c:10]([CH2:11][c:12]3[cH:13][cH:14][c:15]([NH:16][c:17]4[cH:18][cH:19][n:20][c:21]([NH2:22])[n:23]4)[cH:24][c:25]3[F:26])[c:27]12 | ([c:8]-[NH;D2;+0:7]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([NH2;D1;+0:7]-[c:8]) | db1d2c86680d6406cfc43d406a7d37a82476d5b9bb83e186c7450e56 | 1 | 1 | CCO.CO.Cl.O.[Na+].[OH-] | 161 |
300,193 | 977,330 | 1,646,022 | [CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][CH2:28][C:29](O)=[O:30])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:32][C:33]([NH2:41])([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:34]>>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[CH:10]=[CH:11][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][CH2:28][C:29](=[O:30])[NH:41][C:33]([CH3:34])([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH3:32])=[CH:17][CH:16]=3)=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2] | null | US09090573B2_1167 | 2,015 | O[C:23]([CH2:22][CH2:21][c:20]1[c:15](-[c:14]2[cH:13][cH:12][c:11](-[c:10]3[cH:9][cH:8][c:7]([C:6]4([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:39][CH2:40]4)[cH:38][cH:37]3)[cH:36][cH:35]2)[o:16][n:17][c:18]1[CH3:19])=[O:24].[NH2:25][C:26]([CH3:27])([CH3:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[o:16][n:17][c:18]([CH3:19])[c:20]4[CH2:21][CH2:22][C:23](=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[cH:35][cH:36]3)[cH:37][cH:38]2)[CH2:39][CH2:40]1 | 0.584435 | CC(C)(N)c1ccccc1.CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CCC(=O)O)cc3)cc2)CC1>>CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CCC(=O)NC(C)(C)c4ccccc4)cc3)cc2)CC1 | CC(C)(N)c1ccccc1.CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CCC(=O)O)cc3)cc2)CC1>>CCOC(=O)C1(c2ccc(-c3ccc(-c4onc(C)c4CCC(=O)NC(C)(C)c4ccccc4)cc3)cc2)CC1 | US09090573B2_1167grants | 3daaaf5f2ec86858ec7090d58ce6583d404cacf994369a5a2f83eb52 | O[C:23]([CH2:22][CH2:21][c:20]1[c:15](-[c:14]2[cH:13][cH:12][c:11](-[c:10]3[cH:9][cH:8][c:7]([C:6]4([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:39][CH2:40]4)[cH:38][cH:37]3)[cH:36][cH:35]2)[o:16][n:17][c:18]1[CH3:19])=[O:24].[NH2:25][C:26]([CH3:27])([CH3:28])[c:29]1[cH:30][cH:31][cH:32][cH:33][cH:34]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6]1([c:7]2[cH:8][cH:9][c:10](-[c:11]3[cH:12][cH:13][c:14](-[c:15]4[o:16][n:17][c:18]([CH3:19])[c:20]4[CH2:21][CH2:22][C:23](=[O:24])[NH:25][C:26]([CH3:27])([CH3:28])[c:29]4[cH:30][cH:31][cH:32][cH:33][cH:34]4)[cH:35][cH:36]3)[cH:37][cH:38]2)[CH2:39][CH2:40]1 | ([C:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[NH;D2;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([NH2;D1;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1) | 5ad7c2cc16d6ee5b57312b54d1398a8d361f2cfad0dc66add676f018 | 1 | 1 | null | 599 |
399,961 | 1,371,252 | null | [N+:1]([C:4]1[C:5]([OH:14])=[C:6]([O:12][CH3:13])[CH:7]=[C:8]([CH:11]=1)[CH:9]=[O:10])([O-:3])=[O:2].[C:15](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C.CCOCC>[CH3:13][O:12][C:6]1[CH:7]=[C:8]([CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=1[O:14][CH3:15])[CH:9]=[O:10] | |f:1.2.3| | US20130131018A1_1540 | 2,013 | CCOCC.CN(C)C=O.I[CH3:15].O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[OH:14].[Cs+].[Cs+]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[O:14][CH3:15] | 0.821767 | CCOCC.CI.CN(C)C=O.COc1cc(C=O)cc([N+](=O)[O-])c1O.O=C([O-])[O-]~[Cs+]~[Cs+]>>COc1cc(C=O)cc([N+](=O)[O-])c1OC | CCOCC.CI.CN(C)C=O.COc1cc(C=O)cc([N+](=O)[O-])c1O.O=C([O-])[O-].[Cs+].[Cs+]>>COc1cc(C=O)cc([N+](=O)[O-])c1OC | US20130131018A1_1540apps | 2d524d256a641f9462252fe3700155b9904ad3c32d90546888d202d5 | CCOCC.CN(C)C=O.I[CH3:15].O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[OH:14].[Cs+].[Cs+] | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:8][c:9]([N+:10](=[O:11])[O-:12])[c:13]1[O:14][CH3:15] | ([CH3;D1;+0:1]-[O;H0;D2;+0:2]-[c:3])>>(I-[CH3;D1;+0:1]).([OH;D1;+0:2]-[c:3]) | 473af55be62b6878ca02586dd3897a58e070e2929e5bc4a91d22f6c2 | 1 | 2 | CCOCC.CN(C)C=O.O=C([O-])[O-].[Cs+].[Cs+] | 62 |
383,472 | 989,378 | null | [Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:42])[CH2:23][C@@H:24]([CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:25][N:26](C)[C:27](=O)OC(C)(C)C)[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22](=[O:42])[CH2:23][C@H:24]([CH2:25][NH:26][CH3:27])[CH2:35][CH:36]3[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]3)[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1 | null | US20100317697A1_0363 | 2,010 | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]([OH:14])([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28]1)[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1.ClCCl.O=C(O)C(F)(F)F>>[CH3:1][NH:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]([OH:14])([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28]1)[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1 | 0.933748 | COCCCCC(O)(c1cccc(Cl)c1)[C@@H]1CCCN(C(=O)C[C@@H](CC2CCCCC2)CN(C)C(=O)OC(C)(C)C)C1.ClCCl.O=C(O)C(F)(F)F>>CNC[C@@H](CC(=O)N1CCC[C@@H](C(O)(CCCCOC)c2cccc(Cl)c2)C1)CC1CCCCC1 | COCCCCC(O)(c1cccc(Cl)c1)[C@@H]1CCCN(C(=O)C[C@@H](CC2CCCCC2)CN(C)C(=O)OC(C)(C)C)C1.ClCCl.O=C(O)C(F)(F)F>>CNC[C@@H](CC(=O)N1CCC[C@@H](C(O)(CCCCOC)c2cccc(Cl)c2)C1)CC1CCCCC1 | US20100317697A1_0363apps | 33dae3d9d64de7f09a1cdd59de6e25548abd39ebf7022e1717aac20a | CC(C)(C)OC(=O)[N:2]([CH3:1])[CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]([OH:14])([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28]1)[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1.ClCCl.O=C(O)C(F)(F)F | [CH3:1][NH:2][CH2:3][C@@H:4]([CH2:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][CH2:11][C@@H:12]([C:13]([OH:14])([CH2:15][CH2:16][CH2:17][CH2:18][O:19][CH3:20])[c:21]2[cH:22][cH:23][cH:24][c:25]([Cl:26])[cH:27]2)[CH2:28]1)[CH2:29][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1 | ([C:2]-[NH;D2;+0:1]-[C;D1;H3:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C;D1;H3:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | ClCCl.O=C(O)C(F)(F)F | 575 |
374,275 | 830,424 | null | C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[N:11][N:12]3[C:17]([CH:18]4[CH2:24][CH:23]5[N:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:20]([CH2:21][CH2:22]5)[CH2:19]4)=[CH:16][CH:15]=[N:14][C:13]=23)[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[C:10]([C:31]3[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=3)=[N:11][N:12]3[C:17]([CH:18]4[CH2:24][CH:23]5[N:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:20]([CH2:21][CH2:22]5)[CH2:19]4)=[CH:16][CH:15]=[N:14][C:13]=23)[CH:6]=[CH:7][CH:8]=1 | null | US20100029657A1_0119 | 2,010 | BrB(Br)Br.C[O:24][c:23]1[cH:22][cH:21][cH:20][c:19](-[c:18]2[c:17]3[n:16][cH:15][cH:14][c:13]([CH:12]4[CH2:11][CH:10]5[N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:7]([CH2:8][CH2:9]5)[CH2:35]4)[n:34]3[n:33][c:26]2-[c:27]2[cH:28][cH:29][n:30][cH:31][cH:32]2)[cH:25]1.ClCCl>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH:7]2[CH2:8][CH2:9][CH:10]1[CH2:11][CH:12]([c:13]1[cH:14][cH:15][n:16][c:17]3[c:18](-[c:19]4[cH:20][cH:21][cH:22][c:23]([OH:24])[cH:25]4)[c:26](-[c:27]4[cH:28][cH:29][n:30][cH:31][cH:32]4)[n:33][n:34]13)[CH2:35]2 | 0.895185 | BrB(Br)Br.CCOC(=O)N1C2CCC1CC(c1ccnc3c(-c4cccc(OC)c4)c(-c4ccncc4)nn13)C2.ClCCl>>CCOC(=O)N1C2CCC1CC(c1ccnc3c(-c4cccc(O)c4)c(-c4ccncc4)nn13)C2 | BrB(Br)Br.CCOC(=O)N1C2CCC1CC(c1ccnc3c(-c4cccc(OC)c4)c(-c4ccncc4)nn13)C2.ClCCl>>CCOC(=O)N1C2CCC1CC(c1ccnc3c(-c4cccc(O)c4)c(-c4ccncc4)nn13)C2 | US20100029657A1_0119apps | 5c3b840c6000f05be4b5901bf192bcc39ef671b3eee9bfa9c824a9ea | BrB(Br)Br.C[O:24][c:23]1[cH:22][cH:21][cH:20][c:19](-[c:18]2[c:17]3[n:16][cH:15][cH:14][c:13]([CH:12]4[CH2:11][CH:10]5[N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:7]([CH2:8][CH2:9]5)[CH2:35]4)[n:34]3[n:33][c:26]2-[c:27]2[cH:28][cH:29][n:30][cH:31][cH:32]2)[cH:25]1.ClCCl | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH:7]2[CH2:8][CH2:9][CH:10]1[CH2:11][CH:12]([c:13]1[cH:14][cH:15][n:16][c:17]3[c:18](-[c:19]4[cH:20][cH:21][cH:22][c:23]([OH:24])[cH:25]4)[c:26](-[c:27]4[cH:28][cH:29][n:30][cH:31][cH:32]4)[n:33][n:34]13)[CH2:35]2 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCl | 48 |
78,385 | 317,342 | 537,956 | [NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:19]([NH2:23])([CH2:21][CH3:22])[CH3:20].[OH-].[Na+]>C(O)CCC>[NH2:1][C:2]1[N:10]=[C:9]([NH:23][CH:19]([CH2:21][CH3:22])[CH3:20])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1 | |f:2.3| | US06329381B1_ | 2,001 | CCCCO.Cl[c:6]1[n:7][c:8]([NH2:9])[c:10]2[n:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[n:22]1.[CH3:1][CH2:2][CH:3]([CH3:4])[NH2:5].[Na+].[OH-]>>[CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][c:6]1[n:7][c:8]([NH2:9])[c:10]2[n:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[n:22]1 | 0.93075 | CCC(C)N.CCCCO.Nc1nc(Cl)nc2c1ncn2Cc1ccccc1.[Na+]~[OH-]>>CCC(C)Nc1nc(N)c2ncn(Cc3ccccc3)c2n1 | CCC(C)N.CCCCO.Nc1nc(Cl)nc2c1ncn2Cc1ccccc1.[Na+].[OH-]>>CCC(C)Nc1nc(N)c2ncn(Cc3ccccc3)c2n1 | US06329381B1_grants | 681b601103a67f1812c9efb8c292ed11fda77c27b96306dc974ec24c | CCCCO.Cl[c:6]1[n:7][c:8]([NH2:9])[c:10]2[n:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[n:22]1.[CH3:1][CH2:2][CH:3]([CH3:4])[NH2:5].[Na+].[OH-] | [CH3:1][CH2:2][CH:3]([CH3:4])[NH:5][c:6]1[n:7][c:8]([NH2:9])[c:10]2[n:11][cH:12][n:13]([CH2:14][c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[c:21]2[n:22]1 | ([#7;a:5]:[c:4]:[#7;a:3]:[c;H0;D3;+0:1](:[#7;a:2])-[NH;D2;+0:7]-[C:6])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[#7;a:3]:[c:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | 0b588855c6f0ec8e6e2a3fd38e0eeb9f125fc40378b70cf60a109be1 | 1 | 1 | CCCCO.[Na+].[OH-] | 578 |
7,252 | 37,214 | 58,320 | [CH3:1][O:2][CH:3]([O:14][CH3:15])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([OH:13])[CH:9]=[C:10]([CH3:12])[CH:11]=1.[CH3:16][N:17]([CH3:21])[C:18](Cl)=[O:19].C(N(CC)CC)C>C1(C)C(C)=CC=CC=1>[CH3:16][N:17]([CH3:21])[C:18](=[O:19])[O:13][C:8]1[CH:9]=[C:10]([CH3:12])[CH:11]=[C:6]([O:5][CH2:4][CH:3]([O:2][CH3:1])[O:14][CH3:15])[CH:7]=1 | null | US04163112_ | 1,979 | CCN(CC)CC.Cc1ccccc1C.Cl[C:13](=[O:14])[N:15]([CH3:16])[CH3:17].[CH3:1][O:2][CH:3]([CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([OH:12])[cH:18]1)[O:19][CH3:20]>>[CH3:1][O:2][CH:3]([CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([O:12][C:13](=[O:14])[N:15]([CH3:16])[CH3:17])[cH:18]1)[O:19][CH3:20] | 0.610638 | CCN(CC)CC.CN(C)C(=O)Cl.COC(COc1cc(C)cc(O)c1)OC.Cc1ccccc1C>>COC(COc1cc(C)cc(OC(=O)N(C)C)c1)OC | CCN(CC)CC.CN(C)C(=O)Cl.COC(COc1cc(C)cc(O)c1)OC.Cc1ccccc1C>>COC(COc1cc(C)cc(OC(=O)N(C)C)c1)OC | US04163112_grants | 1112ce93783cd39025557a172176e96079939474bbd031beace36510 | CCN(CC)CC.Cc1ccccc1C.Cl[C:13](=[O:14])[N:15]([CH3:16])[CH3:17].[CH3:1][O:2][CH:3]([CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([OH:12])[cH:18]1)[O:19][CH3:20] | [CH3:1][O:2][CH:3]([CH2:4][O:5][c:6]1[cH:7][c:8]([CH3:9])[cH:10][c:11]([O:12][C:13](=[O:14])[N:15]([CH3:16])[CH3:17])[cH:18]1)[O:19][CH3:20] | ([#7:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](-[#7:2])=[O;D1;H0:3]).([OH;D1;+0:4]-[c:5]) | d62d2a2013809b8a4b8434e400eafcf093481a0a444021ef5ad3a5a6 | 1 | 1 | CCN(CC)CC.Cc1ccccc1C | 425 |
264,692 | 871,290 | 1,450,418 | [BH4-].[Na+].[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][C:25](=[O:27])[CH3:26])[CH2:19][CH2:18]2)[CH:12]=3)[CH2:5][CH2:4]1>C(O)C>[CH:3]1([CH2:6][O:7][C:8]2[CH:9]=[CH:10][C:11]3[C:15]([CH:16]=2)=[N:14][N:13]([C@H:17]2[CH2:22][CH2:21][C@H:20]([CH2:23][CH2:24][CH:25]([OH:27])[CH3:26])[CH2:19][CH2:18]2)[CH:12]=3)[CH2:5][CH2:4]1 | |f:0.1| | US08703758B2_1580 | 2,014 | CCO.[BH4-].[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20]4)[cH:21][c:22]3[n:23]2)[CH2:24][CH2:25]1.[Na+]>>[CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20]4)[cH:21][c:22]3[n:23]2)[CH2:24][CH2:25]1 | 0.948723 | CC(=O)CC[C@@H]1CC[C@@H](n2cc3ccc(OCC4CC4)cc3n2)CC1.CCO.[BH4-]~[Na+]>>CC(O)CC[C@@H]1CC[C@@H](n2cc3ccc(OCC4CC4)cc3n2)CC1 | CC(=O)CC[C@@H]1CC[C@@H](n2cc3ccc(OCC4CC4)cc3n2)CC1.CCO.[BH4-].[Na+]>>CC(O)CC[C@@H]1CC[C@@H](n2cc3ccc(OCC4CC4)cc3n2)CC1 | US08703758B2_1580grants | 132d05ff003257721d91c31d0847483ec921b4648ae54147b326a187 | CCO.[BH4-].[CH3:1][C:2](=[O:3])[CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20]4)[cH:21][c:22]3[n:23]2)[CH2:24][CH2:25]1.[Na+] | [CH3:1][CH:2]([OH:3])[CH2:4][CH2:5][C@H:6]1[CH2:7][CH2:8][C@H:9]([n:10]2[cH:11][c:12]3[cH:13][cH:14][c:15]([O:16][CH2:17][CH:18]4[CH2:19][CH2:20]4)[cH:21][c:22]3[n:23]2)[CH2:24][CH2:25]1 | ([C:1]-[CH;D3;+0:2](-[C;D1;H3:3])-[OH;D1;+0:4])>>([C:1]-[C;H0;D3;+0:2](-[C;D1;H3:3])=[O;H0;D1;+0:4]) | 0fb396942a5bc824558e6936c3618c2e342b489a89eccebed032da69 | 1 | 1 | CCO.[BH4-].[Na+] | 91 |
317,873 | 1,032,582 | 1,748,123 | [C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[NH:9][C:10](=[O:19])[C:11]([C:14]([O:16]CC)=[O:15])=[CH:12][N:13]=2)=[CH:3][CH:2]=1.[OH-].[Na+]>CO.O1CCOCC1>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]=[CH:3][C:4]([NH:7][C:8]2[NH:9][C:10](=[O:19])[C:11]([C:14]([OH:16])=[O:15])=[CH:12][N:13]=2)=[CH:5][CH:6]=1 | |f:1.2| | US09309232B2_0118 | 2,016 | C1COCCO1.CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[nH:21][c:22]1=[O:23].CO.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[nH:21][c:22]1=[O:23] | 0.890633 | C1COCCO1.CCOC(=O)c1cnc(Nc2ccc(-c3ccccc3)cc2)[nH]c1=O.CO.[Na+]~[OH-]>>O=C(O)c1cnc(Nc2ccc(-c3ccccc3)cc2)[nH]c1=O | C1COCCO1.CCOC(=O)c1cnc(Nc2ccc(-c3ccccc3)cc2)[nH]c1=O.CO.[Na+].[OH-]>>O=C(O)c1cnc(Nc2ccc(-c3ccccc3)cc2)[nH]c1=O | US09309232B2_0118grants | 321f45353504f3a3250a27a85b9ab3a56616e5002b761401b3e3e840 | C1COCCO1.CC[O:3][C:2](=[O:1])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[nH:21][c:22]1=[O:23].CO.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[cH:5][n:6][c:7]([NH:8][c:9]2[cH:10][cH:11][c:12](-[c:13]3[cH:14][cH:15][cH:16][cH:17][cH:18]3)[cH:19][cH:20]2)[nH:21][c:22]1=[O:23] | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b8d35231a9d964a0bcde41cb860d8e6c4726c2823ff5946d3ed0c3c9 | 1 | 1 | C1COCCO1.CO.[Na+].[OH-] | 171 |
7,421 | 38,081 | 60,073 | [OH-].[Na+].O.[CH3:4]/[C:5](/[CH:11]=[CH:12]/[C:13](/[F:26])=[C:14](\[CH3:25])/[CH:15]=[CH:16]/[C:17]1[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:18]=1[CH3:24])=[CH:6]\[C:7]([O:9]C)=[O:8].Cl>C(O)C>[CH3:4]/[C:5](/[CH:11]=[CH:12]/[C:13](/[F:26])=[C:14](\[CH3:25])/[CH:15]=[CH:16]/[C:17]1[C:21]([CH3:22])=[C:20]([CH3:23])[S:19][C:18]=1[CH3:24])=[CH:6]\[C:7]([OH:9])=[O:8] | |f:0.1| | US04171318_ | 1,979 | CCO.C[O:22][C:20](/[CH:19]=[C:17](/[CH:16]=[CH:15]/[C:13](=[C:2]([CH3:1])/[CH:3]=[CH:4]/[c:5]1[c:6]([CH3:7])[s:8][c:9]([CH3:10])[c:11]1[CH3:12])[F:14])[CH3:18])=[O:21].Cl.O.[Na+].[OH-]>>[CH3:1][C:2](/[CH:3]=[CH:4]/[c:5]1[c:6]([CH3:7])[s:8][c:9]([CH3:10])[c:11]1[CH3:12])=[C:13]([F:14])\[CH:15]=[CH:16]\[C:17]([CH3:18])=[CH:19]\[C:20](=[O:21])[OH:22] | 0.902036 | CCO.COC(=O)/C=C(C)/C=C/C(F)=C(C)/C=C/c1c(C)sc(C)c1C.Cl.O.[Na+]~[OH-]>>CC(/C=C/C(F)=C(C)/C=C/c1c(C)sc(C)c1C)=C\C(=O)O | CCO.COC(=O)/C=C(C)/C=C/C(F)=C(C)/C=C/c1c(C)sc(C)c1C.Cl.O.[Na+].[OH-]>>CC(/C=C/C(F)=C(C)/C=C/c1c(C)sc(C)c1C)=C\C(=O)O | US04171318_grants | 212ed17793b6a44423964d212ef7d716013ac21972ae2f9f9c58dfeb | CCO.C[O:22][C:20](/[CH:19]=[C:17](/[CH:16]=[CH:15]/[C:13](=[C:2]([CH3:1])/[CH:3]=[CH:4]/[c:5]1[c:6]([CH3:7])[s:8][c:9]([CH3:10])[c:11]1[CH3:12])[F:14])[CH3:18])=[O:21].Cl.O.[Na+].[OH-] | [CH3:1][C:2](/[CH:3]=[CH:4]/[c:5]1[c:6]([CH3:7])[s:8][c:9]([CH3:10])[c:11]1[CH3:12])=[C:13]([F:14])\[CH:15]=[CH:16]\[C:17]([CH3:18])=[CH:19]\[C:20](=[O:21])[OH:22] | ([C:5]=[C:4]/[C:2](=[O;D1;H0:3])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])/[C:4]=[C:5]) | 16a2ddd09077ae8eee575ab66345f00875cebad2569c46d80e48757f | 1 | 1 | CCO.Cl.O.[Na+].[OH-] | 58 |
163,103 | 575,246 | 958,611 | [OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=O.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)(O)[O-].[Na+]>ClCCl.C(O)(=O)C>[CH2:10]([NH:17][C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[OH:1])=[O:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1 | |f:2.3| | US07666848B2_0269 | 2,010 | CC(=O)O.ClCCl.O=C([O-])O.O[C:2](=[O:1])[c:11]1[s:12][cH:13][cH:14][c:15]1[OH:16].[NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[Na+]>>[O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[s:12][cH:13][cH:14][c:15]1[OH:16] | 0.854587 | CC(=O)O.ClCCl.NCc1ccccc1.O=C(O)c1sccc1O.O=C([O-])O~[Na+]>>O=C(NCc1ccccc1)c1sccc1O | CC(=O)O.ClCCl.NCc1ccccc1.O=C(O)c1sccc1O.O=C([O-])O.[Na+]>>O=C(NCc1ccccc1)c1sccc1O | US07666848B2_0269grants | af2356015d3652ad1788bc66dc208ccc953efd660fb8310fddf3d140 | CC(=O)O.ClCCl.O=C([O-])O.O[C:2](=[O:1])[c:11]1[s:12][cH:13][cH:14][c:15]1[OH:16].[NH2:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1.[Na+] | [O:1]=[C:2]([NH:3][CH2:4][c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[c:11]1[s:12][cH:13][cH:14][c:15]1[OH:16] | ([#16;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:5]-[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[c:12]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#16;a:4]).([NH2;D1;+0:5]-[C:6]-[c:7]1:[c:8]:[c:9]:[c:10]:[c:11]:[c:12]:1) | 946c3762a80870827e1ce4721f1ddef9fdc67f88aa421ae25921d0fa | 1 | 1 | CC(=O)O.ClCCl.O=C([O-])O.[Na+] | 950 |
275,750 | 904,498 | 1,508,067 | [C:1]1([C:7]2([CH2:13][CH2:14][CH2:15][C:16]([O:18]CC)=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>CO>[C:1]1([C:7]2([CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1 | |f:1.2| | US08822510B2_0358 | 2,014 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.CO.Cl.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | 0.83126 | CCOC(=O)CCCC1(c2ccccc2)CCCCC1.CO.Cl.[Na+]~[OH-]>>O=C(O)CCCC1(c2ccccc2)CCCCC1 | CCOC(=O)CCCC1(c2ccccc2)CCCCC1.CO.Cl.[Na+].[OH-]>>O=C(O)CCCC1(c2ccccc2)CCCCC1 | US08822510B2_0358grants | 3783c36734bd90be6549130c543d1cb6cd23ca35f83e9af837764064 | CC[O:3][C:2](=[O:1])[CH2:4][CH2:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1.CO.Cl.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[CH2:4][CH2:5][CH2:6][C:7]1([c:8]2[cH:9][cH:10][cH:11][cH:12][cH:13]2)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 9a4c5ceadb3b4a753bb8f03491f138cd875a84f1d327e818237f90df | 1 | 1 | CO.Cl.[Na+].[OH-] | 7 |
383,352 | 986,013 | null | [N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]([OH:15])=O)=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH2:20].C(N(CC)CC)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[CH3:16][N:17]([CH3:21])[CH2:18][CH2:19][NH:20][C:13]([C:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[NH:10][N:9]=1)=[O:15] | |f:3.4| | US20100311965A1_0385 | 2,010 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.O.O[C:7](=[O:8])[c:9]1[n:10][nH:11][c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]12.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6].c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][nH:11][c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]12 | 0.698591 | CCN(CC)CC.CN(C)C=O.CN(C)CCN.F[P-](F)(F)(F)(F)F~c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1.O.O=C(O)c1n[nH]c2cc([N+](=O)[O-])ccc12>>CN(C)CCNC(=O)c1n[nH]c2cc([N+](=O)[O-])ccc12 | CCN(CC)CC.CN(C)C=O.CN(C)CCN.F[P-](F)(F)(F)(F)F.O.O=C(O)c1n[nH]c2cc([N+](=O)[O-])ccc12.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1>>CN(C)CCNC(=O)c1n[nH]c2cc([N+](=O)[O-])ccc12 | US20100311965A1_0385apps | 1e49d649487b6fed0fb575a79a2b468359345e0114292987660721c7 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.O.O[C:7](=[O:8])[c:9]1[n:10][nH:11][c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]12.[CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH2:6].c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | [CH3:1][N:2]([CH3:3])[CH2:4][CH2:5][NH:6][C:7](=[O:8])[c:9]1[n:10][nH:11][c:12]2[cH:13][c:14]([N+:15](=[O:16])[O-:17])[cH:18][cH:19][c:20]12 | ([#7;a:5]:[#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[NH;D2;+0:7]-[C:6])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]:[#7;a:5]).([C:6]-[NH2;D1;+0:7]) | edbf0be6af4347c7912e07e17eaca01320754051d4552771ed0794d7 | 1 | 1 | CCN(CC)CC.CN(C)C=O.F[P-](F)(F)(F)(F)F.O.c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1 | 816 |
146,050 | 523,719 | 877,882 | [OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[N:7][C:8]=1[CH3:9].[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][O:1][CH2:2][C:3]2[CH:4]=[CH:5][C:6]([NH:10][C:11](=[O:16])[C:12]([CH3:13])([CH3:15])[CH3:14])=[N:7][C:8]=2[CH3:9])=[CH:20][CH:19]=1 | null | US07482341B2_0544 | 2,009 | Br[CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1.[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH2:15][OH:16]>>[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH2:15][O:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1 | 0.582047 | Cc1nc(NC(=O)C(C)(C)C)ccc1CO.Fc1ccc(CBr)cc1>>Cc1nc(NC(=O)C(C)(C)C)ccc1COCc1ccc(F)cc1 | Cc1nc(NC(=O)C(C)(C)C)ccc1CO.Fc1ccc(CBr)cc1>>Cc1nc(NC(=O)C(C)(C)C)ccc1COCc1ccc(F)cc1 | US07482341B2_0544grants | e15384d61c64d7a857740b2250e23cb45a08784d8de774ad259467ae | Br[CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1.[CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH2:15][OH:16] | [CH3:1][c:2]1[n:3][c:4]([NH:5][C:6](=[O:7])[C:8]([CH3:9])([CH3:10])[CH3:11])[cH:12][cH:13][c:14]1[CH2:15][O:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([F:22])[cH:23][cH:24]1 | ([C:3]-[O;H0;D2;+0:4]-[CH2;D2;+0:1]-[c:2])>>(Br-[CH2;D2;+0:1]-[c:2]).([C:3]-[OH;D1;+0:4]) | 701cdfdda3ad4b079558ae8f26ac582ff4b30dfe8686db2b01ac2d32 | 0.5 | 2 | null | 464 |
125,272 | 461,456 | 781,020 | C([O:5][C:6](=[O:35])[CH2:7][O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([C:17]1[CH:22]=[N:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:19]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:18]=1)[CH:14]([CH3:16])[CH3:15])(C)(C)C.[OH-].[Na+]>CO>[C:23]1([C:20]2[N:21]=[CH:22][C:17]([N:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:6]([OH:35])=[O:5])[CH:14]([CH3:16])[CH3:15])=[N:18][C:19]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1 | |f:1.2| | US07205302B2_0442 | 2,007 | CC(C)(C)[O:13][C:11]([CH2:10][O:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[c:14]1[cH:15][n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[n:31]1)=[O:12].CO.[Na+].[OH-]>>[CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11](=[O:12])[OH:13])[c:14]1[cH:15][n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[n:31]1 | 0.755204 | CC(C)N(CCCCOCC(=O)OC(C)(C)C)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.CO.[Na+]~[OH-]>>CC(C)N(CCCCOCC(=O)O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | CC(C)N(CCCCOCC(=O)OC(C)(C)C)c1cnc(-c2ccccc2)c(-c2ccccc2)n1.CO.[Na+].[OH-]>>CC(C)N(CCCCOCC(=O)O)c1cnc(-c2ccccc2)c(-c2ccccc2)n1 | US07205302B2_0442grants | f5fad1c7fc772dcd182c6c001a238ee57ac155218b8ba934d62ed40c | CC(C)(C)[O:13][C:11]([CH2:10][O:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH:2]([CH3:1])[CH3:3])[c:14]1[cH:15][n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[n:31]1)=[O:12].CO.[Na+].[OH-] | [CH3:1][CH:2]([CH3:3])[N:4]([CH2:5][CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11](=[O:12])[OH:13])[c:14]1[cH:15][n:16][c:17](-[c:18]2[cH:19][cH:20][cH:21][cH:22][cH:23]2)[c:24](-[c:25]2[cH:26][cH:27][cH:28][cH:29][cH:30]2)[n:31]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | cd4c8dfb74ae00d4ec8387e8837370d2f9fd4ad5e54ff56c9878f839 | 1 | 1 | CO.[Na+].[OH-] | 278 |
355,866 | 557,034 | null | [CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][N:12]=1.[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][C:6]1[C:7]([O:9][CH3:10])=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][N:12]=2)[CH:5]=1 | null | US20080070960A1_0260 | 2,008 | Br[Br:20].ClC(Cl)Cl.[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][cH:19]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[Br:20] | 0.503245 | BrBr.COc1ccc(-c2noc3ccccc23)c(OC)c1.ClC(Cl)Cl>>COc1cc(OC)c(-c2noc3ccccc23)cc1Br | BrBr.COc1ccc(-c2noc3ccccc23)c(OC)c1.ClC(Cl)Cl>>COc1cc(OC)c(-c2noc3ccccc23)cc1Br | US20080070960A1_0260apps | 06c02ae80d5310c0b3223d27cda505a1b8129759547d34d1c8e7d6d4 | Br[Br:20].ClC(Cl)Cl.[CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][cH:19]1 | [CH3:1][O:2][c:3]1[cH:4][c:5]([O:6][CH3:7])[c:8](-[c:9]2[n:10][o:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]23)[cH:18][c:19]1[Br:20] | ([Br;H0;D1;+0:1]-[c;H0;D3;+0:3](:[c:2]):[c:4])>>(Br-[Br;H0;D1;+0:1]).([c:2]:[cH;D2;+0:3]:[c:4]) | d6d40ee9982f41488f9d4f37bc30409025fbbda89ae319dea876f903 | 1 | 1 | ClC(Cl)Cl | 98 |
64,930 | 272,186 | 461,829 | [CH2:1](Cl)[CH2:2]Cl.[C:5]([C:8]1C=C[C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25]C=CC=3C[C:12]=2[CH:28]=1)(O)=[O:6].Cl.Cl.[CH3:31][NH:32][CH2:33][C:34]1[NH:35][C:36]2[CH:42]=[CH:41][CH:40]=[CH:39][C:37]=2[N:38]=1.[CH:43]1[CH:44]=CC2N(O)N=N[C:47]=2[CH:48]=1.O.C(N(C(C)C)CC)(C)C>CN(C=O)C>[NH:38]1[C:37]2[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=2[N:35]=[C:34]1[CH2:33][N:32]([CH3:31])[C:5]([C:8]1[CH:28]=[CH:12][C:11]2[CH2:17][CH:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:15]3[CH:24]=[CH:25][CH:44]=[CH:43][C:48]=3[CH2:47][C:1]=2[CH:2]=1)=[O:6] | |f:2.3.4| | US06008213_ | 1,999 | CCN(C(C)C)C(C)C.CN(C)C=O.Cl.Cl.ClCCCl.O.O[C:13]([c:12]1[cH:11][cH:10][c:9]2[c:28]([cH:27]1)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][c:35]1[CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8]2)=[O:14].On1nnc2ccccc21.[NH:15]([CH3:16])[CH2:17][c:18]1[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[nH:26]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]([CH3:16])[CH2:17][c:18]3[n:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]4[nH:26]3)[cH:27][c:28]2[CH2:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21 | 0.868374 | CCN(C(C)C)C(C)C.CCOC(=O)CC1Cc2ccc(C(=O)O)cc2Cc2ccccc21.CN(C)C=O.CNCc1nc2ccccc2[nH]1~Cl~Cl.ClCCCl.O.On1nnc2ccccc21>>CCOC(=O)CC1Cc2ccc(C(=O)N(C)Cc3nc4ccccc4[nH]3)cc2Cc2ccccc21 | CCN(C(C)C)C(C)C.CCOC(=O)CC1Cc2ccc(C(=O)O)cc2Cc2ccccc21.CN(C)C=O.CNCc1nc2ccccc2[nH]1.Cl.Cl.ClCCCl.O.On1nnc2ccccc21>>CCOC(=O)CC1Cc2ccc(C(=O)N(C)Cc3nc4ccccc4[nH]3)cc2Cc2ccccc21 | US06008213_grants | 7ff4b951563cb57c5c9cabbdce8e4b0416f15fd2dff9142205a4960a | CCN(C(C)C)C(C)C.CN(C)C=O.Cl.Cl.ClCCCl.O.O[C:13]([c:12]1[cH:11][cH:10][c:9]2[c:28]([cH:27]1)[CH2:29][c:30]1[cH:31][cH:32][cH:33][cH:34][c:35]1[CH:7]([CH2:6][C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:8]2)=[O:14].On1nnc2ccccc21.[NH:15]([CH3:16])[CH2:17][c:18]1[n:19][c:20]2[cH:21][cH:22][cH:23][cH:24][c:25]2[nH:26]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][c:9]2[cH:10][cH:11][c:12]([C:13](=[O:14])[N:15]([CH3:16])[CH2:17][c:18]3[n:19][c:20]4[cH:21][cH:22][cH:23][cH:24][c:25]4[nH:26]3)[cH:27][c:28]2[CH2:29][c:30]2[cH:31][cH:32][cH:33][cH:34][c:35]21 | ([C:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | 11438d3fa968bbd8c4f3372ffee303c561281eed4a1be36b1ce3c5b0 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.Cl.Cl.ClCCCl.O.On1nnc2ccccc21 | 44 |
358,753 | 603,605 | null | [F:1][C:2]1([F:24])[CH2:7][CH2:6][CH:5]([CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:20])[O:18][CH3:19])=[CH:12][C:11]=2[N+:21]([O-])=O)[CH2:4][CH2:3]1.FSI>CCOC(C)=O.[Pd]>[NH2:21][C:11]1[CH:12]=[C:13]([NH:16][C:17](=[O:20])[O:18][CH3:19])[CH:14]=[CH:15][C:10]=1[NH:9][CH2:8][CH:5]1[CH2:6][CH2:7][C:2]([F:24])([F:1])[CH2:3][CH2:4]1 | null | US20080207612A1_0210 | 2,008 | CCOC(C)=O.FSI.O=[N+:21]([O-])[c:20]1[c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18][CH2:19]2)[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:22]1.[Pd]>>[CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18][CH2:19]2)[c:20]([NH2:21])[cH:22]1 | 0.570766 | CCOC(C)=O.COC(=O)Nc1ccc(NCC2CCC(F)(F)CC2)c([N+](=O)[O-])c1.FSI.[Pd]>>COC(=O)Nc1ccc(NCC2CCC(F)(F)CC2)c(N)c1 | CCOC(C)=O.COC(=O)Nc1ccc(NCC2CCC(F)(F)CC2)c([N+](=O)[O-])c1.FSI.[Pd]>>COC(=O)Nc1ccc(NCC2CCC(F)(F)CC2)c(N)c1 | US20080207612A1_0210apps | 056caa9037ff44700266733945683221b3c31ae7edb3857f0df50ed8 | CCOC(C)=O.FSI.O=[N+:21]([O-])[c:20]1[c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18][CH2:19]2)[cH:8][cH:7][c:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[cH:22]1.[Pd] | [CH3:1][O:2][C:3](=[O:4])[NH:5][c:6]1[cH:7][cH:8][c:9]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][C:15]([F:16])([F:17])[CH2:18][CH2:19]2)[c:20]([NH2:21])[cH:22]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CCOC(C)=O.FSI.[Pd] | 1 |
11,242 | 57,140 | 92,980 | [OH:1][CH2:2][C:3]1[N:4]=[CH:5][N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[C:10](=[O:17])[N:9]3[CH2:18][CH2:19][CH2:20][C@H:8]3[C:7]=12>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[O:17]=[C:10]1[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:6]2[CH:5]=[N:4][C:3]([CH:2]=[O:1])=[C:7]2[C@@H:8]2[CH2:20][CH2:19][CH2:18][N:9]12 | |f:2.3.4| | US04316839_ | 1,982 | ClCCl.[Mn+4].[O-2].[O-2].[OH:1][CH2:2][c:3]1[n:4][cH:5][n:6]2[c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-2>>[O:1]=[CH:2][c:3]1[n:4][cH:5][n:6]2[c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-2 | 0.986043 | ClCCl.O=C1c2ccccc2-n2cnc(CO)c2[C@@H]2CCCN12.[Mn+4]~[O-2]~[O-2]>>O=Cc1ncn2c1[C@@H]1CCCN1C(=O)c1ccccc1-2 | ClCCl.O=C1c2ccccc2-n2cnc(CO)c2[C@@H]2CCCN12.[Mn+4].[O-2].[O-2]>>O=Cc1ncn2c1[C@@H]1CCCN1C(=O)c1ccccc1-2 | US04316839_grants | 56804ba12d7d1ffb92621b4209803e957bc5713ec44717fa4cf674f7 | ClCCl.[Mn+4].[O-2].[O-2].[OH:1][CH2:2][c:3]1[n:4][cH:5][n:6]2[c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-2 | [O:1]=[CH:2][c:3]1[n:4][cH:5][n:6]2[c:7]1[C@@H:8]1[CH2:9][CH2:10][CH2:11][N:12]1[C:13](=[O:14])[c:15]1[cH:16][cH:17][cH:18][cH:19][c:20]1-2 | ([#7;a:1]:[c:2](-[CH;D2;+0:3]=[O;H0;D1;+0:4]):[c:5]:[#7;a:6])>>([#7;a:1]:[c:2](-[CH2;D2;+0:3]-[OH;D1;+0:4]):[c:5]:[#7;a:6]) | 1f2fbaaf61ae958e03167ccb7990c09c0994b1c6e4e7bd9ab5e14ae7 | 1 | 1 | ClCCl.[Mn+4].[O-2].[O-2] | 287 |
17,900 | 87,214 | 142,277 | OO.[CH3:3]C(C1C=CC(OC(C)C(O)=O)=CC=1)=C.[OH:18][C:19]1[CH:30]=[CH:29][C:22]([O:23][CH:24]([CH3:28])[C:25]([OH:27])=[O:26])=[CH:21][CH:20]=1>CO>[OH:18][C:19]1[CH:20]=[CH:21][C:22]([O:23][CH:24]([CH3:28])[C:25]([O:27][CH3:3])=[O:26])=[CH:29][CH:30]=1 | null | US04568497_ | 1,986 | C=C(C)c1ccc(OC(C)C(=O)O)cc1.OO.O[CH3:1].[OH:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1>>[CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1 | 0.704873 | C=C(C)c1ccc(OC(C)C(=O)O)cc1.CC(Oc1ccc(O)cc1)C(=O)O.CO.OO>>COC(=O)C(C)Oc1ccc(O)cc1 | C=C(C)c1ccc(OC(C)C(=O)O)cc1.CC(Oc1ccc(O)cc1)C(=O)O.CO.OO>>COC(=O)C(C)Oc1ccc(O)cc1 | US04568497_grants | 4bc3928e3b60d517360d12521fc8c4eee3b58407cb2546958d443a89 | C=C(C)c1ccc(OC(C)C(=O)O)cc1.OO.O[CH3:1].[OH:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1 | [CH3:1][O:2][C:3](=[O:4])[CH:5]([CH3:6])[O:7][c:8]1[cH:9][cH:10][c:11]([OH:12])[cH:13][cH:14]1 | ([CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3]=[O;D1;H0:2])>>(O-[CH3;D1;+0:1]).([O;D1;H0:2]=[C:3]-[OH;D1;+0:4]) | e189425e090fce77131c907ebf1468461240dd27d4457a40d701e43e | 1 | 1 | C=C(C)c1ccc(OC(C)C(=O)O)cc1.OO | 195 |
183,694 | 636,261 | 1,052,127 | [Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[CH:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[CH3:19][NH2:20]>C1(C)C=CC=CC=1.C1COCC1.O>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[CH:10]=[C:9]([CH2:11][NH:20][CH3:19])[S:8][C:6]=2[N:7]=1 | null | US07888352B2_0249 | 2,011 | C1CCOC1.Cc1ccccc1.O.O=[CH:3][c:4]1[cH:5][c:6]2[c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]([Cl:16])[n:17][c:18]2[s:19]1.[CH3:1][NH2:2]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]([Cl:16])[n:17][c:18]2[s:19]1 | 0.97072 | C1CCOC1.CN.Cc1ccccc1.O.O=Cc1cc2c(N3CCOCC3)nc(Cl)nc2s1>>CNCc1cc2c(N3CCOCC3)nc(Cl)nc2s1 | C1CCOC1.CN.Cc1ccccc1.O.O=Cc1cc2c(N3CCOCC3)nc(Cl)nc2s1>>CNCc1cc2c(N3CCOCC3)nc(Cl)nc2s1 | US07888352B2_0249grants | b5b5461e0b9b6bacfc489fedc0cc943f89f862ac4d8f7e223e1d504a | C1CCOC1.Cc1ccccc1.O.O=[CH:3][c:4]1[cH:5][c:6]2[c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]([Cl:16])[n:17][c:18]2[s:19]1.[CH3:1][NH2:2] | [CH3:1][NH:2][CH2:3][c:4]1[cH:5][c:6]2[c:7]([N:8]3[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)[n:14][c:15]([Cl:16])[n:17][c:18]2[s:19]1 | ([#16;a:3]:[c:2]-[CH2;D2;+0:1]-[NH;D2;+0:5]-[C;D1;H3:4])>>(O=[CH;D2;+0:1]-[c:2]:[#16;a:3]).([C;D1;H3:4]-[NH2;D1;+0:5]) | af4774f2f134db03c6e9fde5c46f39134bb6e007fa292317009cd468 | 1 | 1 | C1CCOC1.Cc1ccccc1.O | 691 |
345,527 | 404,563 | null | [CH3:1][C:2]1[N:3]=[C:4]([C:7]2([N:13]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:16])[CH3:15])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[S:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH:29]1([CH2:32]Br)[CH2:31][CH2:30]1.C(OCC)(=O)C>CN(C)C=O>[CH:29]1([CH2:32][N:10]2[CH2:11][CH2:12][C:7]([N:13]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:14](=[O:16])[CH3:15])([C:4]3[S:5][CH:6]=[C:2]([CH3:1])[N:3]=3)[CH2:8][CH2:9]2)[CH2:31][CH2:30]1 | |f:1.2.3| | US20060252797A1_0528 | 2,006 | Br[CH2:21][CH:22]1[CH2:23][CH2:24]1.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1([c:12]2[n:13][c:14]([CH3:15])[cH:16][s:17]2)[CH2:18][CH2:19][NH:20][CH2:25][CH2:26]1.[K+].[K+]>>[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1([c:12]2[n:13][c:14]([CH3:15])[cH:16][s:17]2)[CH2:18][CH2:19][N:20]([CH2:21][CH:22]2[CH2:23][CH2:24]2)[CH2:25][CH2:26]1 | 0.886415 | BrCC1CC1.CC(=O)N(c1ccccc1)C1(c2nc(C)cs2)CCNCC1.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-]~[K+]~[K+]>>CC(=O)N(c1ccccc1)C1(c2nc(C)cs2)CCN(CC2CC2)CC1 | BrCC1CC1.CC(=O)N(c1ccccc1)C1(c2nc(C)cs2)CCNCC1.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[K+].[K+]>>CC(=O)N(c1ccccc1)C1(c2nc(C)cs2)CCN(CC2CC2)CC1 | US20060252797A1_0528apps | d484d4685724dee7d988fc35320932bdc027ab80c9661b52162c57b7 | Br[CH2:21][CH:22]1[CH2:23][CH2:24]1.CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1([c:12]2[n:13][c:14]([CH3:15])[cH:16][s:17]2)[CH2:18][CH2:19][NH:20][CH2:25][CH2:26]1.[K+].[K+] | [CH3:1][C:2](=[O:3])[N:4]([c:5]1[cH:6][cH:7][cH:8][cH:9][cH:10]1)[C:11]1([c:12]2[n:13][c:14]([CH3:15])[cH:16][s:17]2)[CH2:18][CH2:19][N:20]([CH2:21][CH:22]2[CH2:23][CH2:24]2)[CH2:25][CH2:26]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 53994dd2d8bb14288cdfb7c2951155e80ca49e2c98f7d531177a38b3 | 0.5 | 2 | CCOC(C)=O.CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 73 |
300,361 | 977,605 | 1,646,431 | [NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[C:11]([CH2:26][CH3:27])=[N:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1.[O:28]1[CH2:33][CH2:32][CH:31]([N:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH2:30][CH2:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O.CO>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[C:11]([CH2:26][CH3:27])=[N:12][CH:13]=[CH:14][C:15]=2[C:16]2[CH:24]=[CH:23][C:19]([C:20]([N:37]3[CH2:36][CH2:35][N:34]([CH:31]4[CH2:32][CH2:33][O:28][CH2:29][CH2:30]4)[CH2:39][CH2:38]3)=[O:21])=[C:18]([F:25])[CH:17]=2)=[CH:4][CH:3]=1 | |f:2.3,6.7| | US09090564B2_0207 | 2,015 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.F[P-](F)(F)(F)(F)F.O.O[C:12]([c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][n:4][c:3]([CH2:2][CH3:1])[c:29]2[C:30]#[C:31][c:32]2[cH:33][cH:34][c:35]([NH2:36])[n:37][cH:38]2)[cH:28][c:26]1[F:27])=[O:13].[NH:14]1[CH2:15][CH2:16][N:17]([CH:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1>>[CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([CH:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[CH2:24][CH2:25]3)[c:26]([F:27])[cH:28]2)[c:29]1[C:30]#[C:31][c:32]1[cH:33][cH:34][c:35]([NH2:36])[n:37][cH:38]1 | 0.780987 | C1CN(C2CCOCC2)CCN1.CCN(C(C)C)C(C)C.CCc1nccc(-c2ccc(C(=O)O)c(F)c2)c1C#Cc1ccc(N)nc1.CN(C)C(On1nnc2cccnc21)=[N+](C)C~F[P-](F)(F)(F)(F)F.CN(C)C=O.CO~O>>CCc1nccc(-c2ccc(C(=O)N3CCN(C4CCOCC4)CC3)c(F)c2)c1C#Cc1ccc(N)nc1 | C1CN(C2CCOCC2)CCN1.CCN(C(C)C)C(C)C.CCc1nccc(-c2ccc(C(=O)O)c(F)c2)c1C#Cc1ccc(N)nc1.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.F[P-](F)(F)(F)(F)F.O>>CCc1nccc(-c2ccc(C(=O)N3CCN(C4CCOCC4)CC3)c(F)c2)c1C#Cc1ccc(N)nc1 | US09090564B2_0207grants | c31dd01c0064610ce41e90a7f9ae9a754246964e5d300241f5b678d8 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.F[P-](F)(F)(F)(F)F.O.O[C:12]([c:11]1[cH:10][cH:9][c:8](-[c:7]2[cH:6][cH:5][n:4][c:3]([CH2:2][CH3:1])[c:29]2[C:30]#[C:31][c:32]2[cH:33][cH:34][c:35]([NH2:36])[n:37][cH:38]2)[cH:28][c:26]1[F:27])=[O:13].[NH:14]1[CH2:15][CH2:16][N:17]([CH:18]2[CH2:19][CH2:20][O:21][CH2:22][CH2:23]2)[CH2:24][CH2:25]1 | [CH3:1][CH2:2][c:3]1[n:4][cH:5][cH:6][c:7](-[c:8]2[cH:9][cH:10][c:11]([C:12](=[O:13])[N:14]3[CH2:15][CH2:16][N:17]([CH:18]4[CH2:19][CH2:20][O:21][CH2:22][CH2:23]4)[CH2:24][CH2:25]3)[c:26]([F:27])[cH:28]2)[c:29]1[C:30]#[C:31][c:32]1[cH:33][cH:34][c:35]([NH2:36])[n:37][cH:38]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 11438d3fa968bbd8c4f3372ffee303c561281eed4a1be36b1ce3c5b0 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C(On1nnc2cccnc21)=[N+](C)C.CN(C)C=O.CO.F[P-](F)(F)(F)(F)F.O | 44 |
32,657 | 149,350 | 239,693 | [CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][C:10]2=[O:13])=[CH:5][CH:4]=1.[Br:14]Br>CCOCC>[Br:14][CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:10]1=[O:13] | null | US05059609_ | 1,991 | Br[Br:12].CCOCC.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:13][CH2:14]2>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH:11]([Br:12])[CH2:13][CH2:14]2 | 0.518475 | BrBr.CCOCC.COc1ccc2c(c1)C(=O)CCC2>>COc1ccc2c(c1)C(=O)C(Br)CC2 | BrBr.CCOCC.COc1ccc2c(c1)C(=O)CCC2>>COc1ccc2c(c1)C(=O)C(Br)CC2 | US05059609_grants | bf043b9b5c2b8393be8c074c1b91ffbfbc03973bb046b1151dc07425 | Br[Br:12].CCOCC.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH2:11][CH2:13][CH2:14]2 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([cH:8]1)[C:9](=[O:10])[CH:11]([Br:12])[CH2:13][CH2:14]2 | ([Br;H0;D1;+0:1]-[CH;D3;+0:3](-[C:2])-[C:4]=[O;D1;H0:5])>>(Br-[Br;H0;D1;+0:1]).([C:2]-[CH2;D2;+0:3]-[C:4]=[O;D1;H0:5]) | 3560772917679e725a1e0eabb8a9da5f9fe63ca45096a51401dd0ce8 | 1 | 1 | CCOCC | 82 |
113,733 | 427,012 | 727,599 | [CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([C:16]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]=5[NH2:25])[NH:18][N:17]=4)[NH:13][C:12]=3[CH:26]=2)[CH2:4][CH2:3]1.[C:27](Cl)(=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:15]=[C:14]([C:16]4[C:24]5[C:19](=[CH:20][CH:21]=[CH:22][C:23]=5[NH:25][C:27](=[O:34])[C:28]5[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=5)[NH:18][N:17]=4)[NH:13][C:12]=3[CH:26]=2)[CH2:4][CH2:3]1 | null | US07064215B2_0796 | 2,006 | CCN(C(C)C)C(C)C.ClCCl.Cl[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[n:10][c:11](-[c:12]4[n:13][nH:14][c:15]5[cH:16][cH:17][cH:18][c:19]([NH2:20])[c:29]45)[nH:30][c:31]3[cH:32]2)[CH2:33][CH2:34]1>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[n:10][c:11](-[c:12]4[n:13][nH:14][c:15]5[cH:16][cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[c:23]6[cH:24][cH:25][cH:26][cH:27][cH:28]6)[c:29]45)[nH:30][c:31]3[cH:32]2)[CH2:33][CH2:34]1 | 0.896219 | CCN(C(C)C)C(C)C.CN1CCN(c2ccc3nc(-c4n[nH]c5cccc(N)c45)[nH]c3c2)CC1.ClCCl.O=C(Cl)c1ccccc1>>CN1CCN(c2ccc3nc(-c4n[nH]c5cccc(NC(=O)c6ccccc6)c45)[nH]c3c2)CC1 | CCN(C(C)C)C(C)C.CN1CCN(c2ccc3nc(-c4n[nH]c5cccc(N)c45)[nH]c3c2)CC1.ClCCl.O=C(Cl)c1ccccc1>>CN1CCN(c2ccc3nc(-c4n[nH]c5cccc(NC(=O)c6ccccc6)c45)[nH]c3c2)CC1 | US07064215B2_0796grants | 4731f0a1419beab3bed303298611fa522dc28c8ce36d1e0b8a604dbe | CCN(C(C)C)C(C)C.ClCCl.Cl[C:21](=[O:22])[c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[n:10][c:11](-[c:12]4[n:13][nH:14][c:15]5[cH:16][cH:17][cH:18][c:19]([NH2:20])[c:29]45)[nH:30][c:31]3[cH:32]2)[CH2:33][CH2:34]1 | [CH3:1][N:2]1[CH2:3][CH2:4][N:5]([c:6]2[cH:7][cH:8][c:9]3[n:10][c:11](-[c:12]4[n:13][nH:14][c:15]5[cH:16][cH:17][cH:18][c:19]([NH:20][C:21](=[O:22])[c:23]6[cH:24][cH:25][cH:26][cH:27][cH:28]6)[c:29]45)[nH:30][c:31]3[cH:32]2)[CH2:33][CH2:34]1 | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 81bbe9d480d200be1437e9ca625a57474abf80dfdc397cf8e383daca | 1 | 1 | CCN(C(C)C)C(C)C.ClCCl | 11 |
198,824 | 679,822 | 1,121,795 | [NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:9](O[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]>C(O)(C)(C)C.O>[C:12]([O:11][C:9]([N:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)=[O:10])([CH3:15])([CH3:14])[CH3:13] | |f:1.2| | US08039463B2_0236 | 2,011 | CC(C)(C)O.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].O.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.[Na+].[OH-]>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | 0.185111 | C1CNCCN1.CC(C)(C)O.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O.[Na+]~[OH-]>>CC(C)(C)OC(=O)N1CCNCC1 | C1CNCCN1.CC(C)(C)O.CC(C)(C)OC(=O)OC(=O)OC(C)(C)C.O.[Na+].[OH-]>>CC(C)(C)OC(=O)N1CCNCC1 | US08039463B2_0236grants | f21b3a9d750dd27397c725fb61fd416d914e8cc3a89bfbc3c29eaf6a | CC(C)(C)O.CC(C)(C)OC(=O)O[C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7].O.[NH:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1.[Na+].[OH-] | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1 | ([C:8]-[N;H0;D3;+0:9](-[C:10])-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7])>>(C-C(-C)(-C)-O-C(=O)-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[#8:3]-[C:4](-[C;D1;H3:5])(-[C;D1;H3:6])-[C;D1;H3:7]).([C:8]-[NH;D2;+0:9]-[C:10]) | 4adaee2f919129a728a81156383c0a0b04988e7bc84e82c9b95523a9 | 1 | 1 | CC(C)(C)O.O.[Na+].[OH-] | 694 |
287,783 | 938,298 | 1,574,148 | [BH4-].[Na+].[C:3]([C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:10]=1[CH2:11][C:12](OC)=[O:13])#[N:4].C(OCC)(=O)C>C(O)C.CCCCCC>[OH:13][CH2:12][CH2:11][C:10]1[C:5]([C:3]#[N:4])=[CH:6][N:7]=[CH:8][CH:9]=1 | |f:0.1| | US08946260B2_0980 | 2,015 | CCCCCC.CCO.CCOC(C)=O.CO[C:10]([CH2:9][c:8]1[c:3]([C:2]#[N:1])[cH:4][n:5][cH:6][cH:7]1)=[O:11].[BH4-].[Na+]>>[N:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][OH:11] | 0.737039 | CCCCCC.CCO.CCOC(C)=O.COC(=O)Cc1ccncc1C#N.[BH4-]~[Na+]>>N#Cc1cnccc1CCO | CCCCCC.CCO.CCOC(C)=O.COC(=O)Cc1ccncc1C#N.[BH4-].[Na+]>>N#Cc1cnccc1CCO | US08946260B2_0980grants | cb0202efdce1819142d3e80ce964a1eddd0f9a713a7a70ae6c35a259 | CCCCCC.CCO.CCOC(C)=O.CO[C:10]([CH2:9][c:8]1[c:3]([C:2]#[N:1])[cH:4][n:5][cH:6][cH:7]1)=[O:11].[BH4-].[Na+] | [N:1]#[C:2][c:3]1[cH:4][n:5][cH:6][cH:7][c:8]1[CH2:9][CH2:10][OH:11] | ([C:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;H0;D1;+0:3]) | ace077327b65885e2493775e77cea5434d2da2918de8308af58629a6 | 1 | 1 | CCCCCC.CCO.CCOC(C)=O.[BH4-].[Na+] | 343 |
48,329 | 210,813 | 340,683 | [CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]([O:25]C(C)(C)C)=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[CH:30]=[C:31]([NH:34][C:35]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:36])[CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>>[CH2:1]([C:5]1[N:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[C:18]([C:23]([OH:25])=[O:24])=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][CH:12]=2)[C:8]2[CH:30]=[C:31]([NH:34][C:35]([CH:37]3[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38]3)=[O:36])[CH:32]=[CH:33][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4] | null | US05541229_ | 1,996 | CC(C)(C)[O:36][C:34]([c:33]1[c:28](-[c:27]2[cH:26][cH:25][c:24]([CH2:23][n:22]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH:14]5[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]5)[cH:20][c:21]43)[cH:38][cH:37]2)[cH:29][cH:30][cH:31][cH:32]1)=[O:35].O=C(O)C(F)(F)F>>[CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]2[n:22]1[CH2:23][c:24]1[cH:25][cH:26][c:27](-[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34](=[O:35])[OH:36])[cH:37][cH:38]1 | 0.870849 | CCCCc1nc2ccc(NC(=O)C3CCCCC3)cc2n1Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1.O=C(O)C(F)(F)F>>CCCCc1nc2ccc(NC(=O)C3CCCCC3)cc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | CCCCc1nc2ccc(NC(=O)C3CCCCC3)cc2n1Cc1ccc(-c2ccccc2C(=O)OC(C)(C)C)cc1.O=C(O)C(F)(F)F>>CCCCc1nc2ccc(NC(=O)C3CCCCC3)cc2n1Cc1ccc(-c2ccccc2C(=O)O)cc1 | US05541229_grants | 7431980af28e6ab094f16837ec2c7d7930057460b3900d7a176c3c38 | CC(C)(C)[O:36][C:34]([c:33]1[c:28](-[c:27]2[cH:26][cH:25][c:24]([CH2:23][n:22]3[c:5]([CH2:4][CH2:3][CH2:2][CH3:1])[n:6][c:7]4[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH:14]5[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]5)[cH:20][c:21]43)[cH:38][cH:37]2)[cH:29][cH:30][cH:31][cH:32]1)=[O:35].O=C(O)C(F)(F)F | [CH3:1][CH2:2][CH2:3][CH2:4][c:5]1[n:6][c:7]2[cH:8][cH:9][c:10]([NH:11][C:12](=[O:13])[CH:14]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]3)[cH:20][c:21]2[n:22]1[CH2:23][c:24]1[cH:25][cH:26][c:27](-[c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]2[C:34](=[O:35])[OH:36])[cH:37][cH:38]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-C(-C)(-C)-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 19099d615ac8e69cee786c921f9ac0f1b45fdfafec5366cce7c8840f | 1 | 1 | O=C(O)C(F)(F)F | 752 |
99,450 | 383,150 | 655,102 | Cl[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.[CH2:22]([NH:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH3:23].O>CS(C)=O.Cl>[CH2:25]([N:24]([CH2:22][CH3:23])[C:2]1[C:3]2[C:11]([CH3:12])=[CH:10][N:9]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH2:26][CH2:27][CH3:28] | null | US06765008B1_ | 2,004 | CS(C)=O.Cl.Cl[c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14]1[c:15]([CH3:16])[cH:17][n:18]2-[c:19]1[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25][c:26]1[CH3:27].O.[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH3:7]>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14]1[c:15]([CH3:16])[cH:17][n:18]2-[c:19]1[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25][c:26]1[CH3:27] | 0.593715 | CCCCNCC.CS(C)=O.Cc1cc(C)c(-n2cc(C)c3c(Cl)nc(C)nc32)c(C)c1.Cl.O>>CCCCN(CC)c1nc(C)nc2c1c(C)cn2-c1c(C)cc(C)cc1C | CCCCNCC.CS(C)=O.Cc1cc(C)c(-n2cc(C)c3c(Cl)nc(C)nc32)c(C)c1.Cl.O>>CCCCN(CC)c1nc(C)nc2c1c(C)cn2-c1c(C)cc(C)cc1C | US06765008B1_grants | c853ad0815c88c7109a79c8d0c1c519ba49605b40f829e3f90829808 | CS(C)=O.Cl.Cl[c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14]1[c:15]([CH3:16])[cH:17][n:18]2-[c:19]1[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25][c:26]1[CH3:27].O.[CH3:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH3:7] | [CH3:1][CH2:2][CH2:3][CH2:4][N:5]([CH2:6][CH3:7])[c:8]1[n:9][c:10]([CH3:11])[n:12][c:13]2[c:14]1[c:15]([CH3:16])[cH:17][n:18]2-[c:19]1[c:20]([CH3:21])[cH:22][c:23]([CH3:24])[cH:25][c:26]1[CH3:27] | ([#7;a:5]:[c:4](:[#7;a:6]):[c:3]:[c;H0;D3;+0:1](:[#7;a:2])-[N;H0;D3;+0:8](-[C:7])-[C:9])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[c:4](:[#7;a:5]):[#7;a:6]).([C:7]-[NH;D2;+0:8]-[C:9]) | 98993a88c10387a914bcf265b944bd72690195732e3c87635ca51ed2 | 1 | 1 | CS(C)=O.Cl.O | 540 |
439,990 | 1,906,961 | null | [CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][C@@H:8]2[C:12]3=[N:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[N:11]3[C:10](=[O:20])[NH:9]2)=[CH:5][CH:4]=1.[NH2:23][C@H:24]1[C@@H:28]([F:29])[CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1>>[NH:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[N:11]=[C:12]1[C@H:8]([NH:9][C:10](=[O:20])[NH:23][C@H:24]1[C@@H:28]([F:29])[CH2:27][N:26]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25]1)[CH2:7][C:6]1[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1 | null | US20160200686A1_1050 | 2,016 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@H:8]2[NH:9][C:10](=[O:11])[n:34]3[c:26]2[n:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]23)[cH:35][cH:36]1.[NH2:12][C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@@H:24]1[F:25]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@@H:8]([NH:9][C:10](=[O:11])[NH:12][C@@H:13]2[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@@H:24]2[F:25])[c:26]2[n:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]3[nH:34]2)[cH:35][cH:36]1 | 0.410879 | CC(C)(C)OC(=O)N1C[C@@H](N)[C@@H](F)C1.COc1ccc(C[C@H]2NC(=O)n3c2nc2ccccc23)cc1>>COc1ccc(C[C@@H](NC(=O)N[C@@H]2CN(C(=O)OC(C)(C)C)C[C@@H]2F)c2nc3ccccc3[nH]2)cc1 | CC(C)(C)OC(=O)N1C[C@@H](N)[C@@H](F)C1.COc1ccc(C[C@H]2NC(=O)n3c2nc2ccccc23)cc1>>COc1ccc(C[C@@H](NC(=O)N[C@@H]2CN(C(=O)OC(C)(C)C)C[C@@H]2F)c2nc3ccccc3[nH]2)cc1 | US20160200686A1_1050apps | f9420e1205f0f4589e00d2109284329ae59e1f40f5fee6982cbfcd15 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@H:8]2[NH:9][C:10](=[O:11])[n:34]3[c:26]2[n:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]23)[cH:35][cH:36]1.[NH2:12][C@@H:13]1[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@@H:24]1[F:25] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][C@@H:8]([NH:9][C:10](=[O:11])[NH:12][C@@H:13]2[CH2:14][N:15]([C:16](=[O:17])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:23][C@@H:24]2[F:25])[c:26]2[n:27][c:28]3[cH:29][cH:30][cH:31][cH:32][c:33]3[nH:34]2)[cH:35][cH:36]1 | ([#7;a:6]1:[c:5]:[nH;D2;+0:4]:[c:8]:[c:7]:1.[#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[NH;D2;+0:10]-[C:9])>>([#7:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[n;H0;D3;+0:4]1:[c:5]:[#7;a:6]:[c:7]:[c:8]:1).([C:9]-[NH2;D1;+0:10]) | 6aac2e4bb8ef45b13343815db02a89dfba182c856929745a52e58075 | 0.5 | 2 | null | 999 |
420,334 | 1,763,137 | null | [CH:1]1([C:4]2[N:5]=[C:6]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[N:7]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:8]=2[C:9]([O:11]CC)=[O:10])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]1([C:4]2[N:5]=[C:6]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[N:7]([CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:8]=2[C:9]([OH:11])=[O:10])[CH2:3][CH2:2]1 | |f:1.2| | US20150284358A1_0154 | 2,015 | C1CCOC1.CC[O:3][C:2](=[O:1])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12.CO.Cl.[Na+].[OH-]>>[O:1]=[C:2]([OH:3])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12 | 0.874485 | C1CCOC1.CCOC(=O)c1c(C2CC2)nc(-c2cccnc2)n1Cc1cccc2ccccc12.CO.Cl.[Na+]~[OH-]>>O=C(O)c1c(C2CC2)nc(-c2cccnc2)n1Cc1cccc2ccccc12 | C1CCOC1.CCOC(=O)c1c(C2CC2)nc(-c2cccnc2)n1Cc1cccc2ccccc12.CO.Cl.[Na+].[OH-]>>O=C(O)c1c(C2CC2)nc(-c2cccnc2)n1Cc1cccc2ccccc12 | US20150284358A1_0154apps | bf4d45d2f059f1a5ceb367dc16c954425a17d313ef299fc46a690373 | C1CCOC1.CC[O:3][C:2](=[O:1])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12.CO.Cl.[Na+].[OH-] | [O:1]=[C:2]([OH:3])[c:4]1[c:5]([CH:6]2[CH2:7][CH2:8]2)[n:9][c:10](-[c:11]2[cH:12][cH:13][cH:14][n:15][cH:16]2)[n:17]1[CH2:18][c:19]1[cH:20][cH:21][cH:22][c:23]2[cH:24][cH:25][cH:26][cH:27][c:28]12 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b8d35231a9d964a0bcde41cb860d8e6c4726c2823ff5946d3ed0c3c9 | 1 | 1 | C1CCOC1.CO.Cl.[Na+].[OH-] | 171 |
226,843 | 759,956 | 1,251,651 | [Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][N:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:16][CH2:17][O:18][C:19]1[C:28]2[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=2)[N:22]=[CH:21][CH:20]=1.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH2:16][CH2:17][O:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][CH:27]=3)[N:22]=[CH:21][CH:20]=2)[N:7]=1 | |f:1.2.3| | US08314087B2_0508 | 2,012 | Br[CH2:10][CH2:9][O:8][c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][c:22]2[n:21][cH:20][cH:19]1.CN(C)C=O.O.O=C([O-])[O-].[K+].[K+].[nH:11]1[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1=[O:18]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([O:8][CH2:9][CH2:10][n:11]3[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3=[O:18])[cH:19][cH:20][n:21][c:22]2[cH:23]1 | 0.970902 | CN(C)C=O.COc1ccc2c(OCCBr)ccnc2c1.O.O=C([O-])[O-]~[K+]~[K+].O=c1ccc(Cl)n[nH]1>>COc1ccc2c(OCCn3nc(Cl)ccc3=O)ccnc2c1 | CN(C)C=O.COc1ccc2c(OCCBr)ccnc2c1.O.O=C([O-])[O-].O=c1ccc(Cl)n[nH]1.[K+].[K+]>>COc1ccc2c(OCCn3nc(Cl)ccc3=O)ccnc2c1 | US08314087B2_0508grants | 585cad20e9152ac2cbfee8d70915c98a9b004722ae3c61c7e90b1bba | Br[CH2:10][CH2:9][O:8][c:7]1[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:23][c:22]2[n:21][cH:20][cH:19]1.CN(C)C=O.O.O=C([O-])[O-].[K+].[K+].[nH:11]1[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]1=[O:18] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]2[c:7]([O:8][CH2:9][CH2:10][n:11]3[n:12][c:13]([Cl:14])[cH:15][cH:16][c:17]3=[O:18])[cH:19][cH:20][n:21][c:22]2[cH:23]1 | ([#7;a:3]:[n;H0;D3;+0:4](:[c:5])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([#7;a:3]:[nH;D2;+0:4]:[c:5]) | 357e7b62b7ce08462d0682ba5ed472fb239475424f9df736b44eb978 | 1 | 1 | CN(C)C=O.O.O=C([O-])[O-].[K+].[K+] | 577 |
278,905 | 913,830 | 1,528,104 | [CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[Br:18]N1C(=O)CCC1=O.CCOC(C)=O>C(Cl)Cl.CC#N>[CH3:1][O:2][C:3]([C:5]1([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[C:15]([Br:18])[CH:16]=2)[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4] | |f:3.4| | US08859602B2_0369 | 2,014 | CC#N.CCOC(C)=O.ClCCl.O=C1CCC(=O)N1[Br:12].[CH3:1][O:2][C:3](=[O:4])[C:5]1([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:13]2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5]1([c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]([Br:12])[cH:13]2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | 0.925741 | CC#N~ClCCl.CCOC(C)=O.COC(=O)C1(c2ccc(N)cc2)CCOCC1.O=C1CCC(=O)N1Br>>COC(=O)C1(c2ccc(N)c(Br)c2)CCOCC1 | CC#N.CCOC(C)=O.COC(=O)C1(c2ccc(N)cc2)CCOCC1.ClCCl.O=C1CCC(=O)N1Br>>COC(=O)C1(c2ccc(N)c(Br)c2)CCOCC1 | US08859602B2_0369grants | dc46911aaf6a73cecdea512993bc9914b6d9d5969054d252a4463aed | CC#N.CCOC(C)=O.ClCCl.O=C1CCC(=O)N1[Br:12].[CH3:1][O:2][C:3](=[O:4])[C:5]1([c:6]2[cH:7][cH:8][c:9]([NH2:10])[cH:11][cH:13]2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | [CH3:1][O:2][C:3](=[O:4])[C:5]1([c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]([Br:12])[cH:13]2)[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1 | ([Br;H0;D1;+0:1]-[c;H0;D3;+0:3](:[c:2]):[c:4])>>(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1]).([c:2]:[cH;D2;+0:3]:[c:4]) | 04aac57316494f5621172b80523cd496e017f4d0104703ad33b2fa4b | 1 | 1 | CC#N.CCOC(C)=O.ClCCl | 4 |
202,260 | 688,845 | 1,136,401 | [F:1][C:2]1[C:3]([F:23])=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=3)[CH3:12])[C:6]=2[CH:22]=1>C1COCC1.[Ni]>[NH2:19][C:15]1[CH:14]=[C:13]([CH:11]([N:7]2[C:6]3[CH:22]=[C:2]([F:1])[C:3]([F:23])=[CH:4][C:5]=3[O:9][C:8]2=[O:10])[CH3:12])[CH:18]=[CH:17][CH:16]=1 | null | US08071593B2_0248 | 2,011 | C1CCOC1.O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]([CH3:1])[n:10]2[c:11](=[O:12])[o:13][c:14]3[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]23)[cH:9]1.[Ni]>>[CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:9]1)[n:10]1[c:11](=[O:12])[o:13][c:14]2[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]12 | 0.979513 | C1CCOC1.CC(c1cccc([N+](=O)[O-])c1)n1c(=O)oc2cc(F)c(F)cc21.[Ni]>>CC(c1cccc(N)c1)n1c(=O)oc2cc(F)c(F)cc21 | C1CCOC1.CC(c1cccc([N+](=O)[O-])c1)n1c(=O)oc2cc(F)c(F)cc21.[Ni]>>CC(c1cccc(N)c1)n1c(=O)oc2cc(F)c(F)cc21 | US08071593B2_0248grants | 5b321e93267ec23ad0f5ff75e7e2a68ae56efa75fd16030062ed5097 | C1CCOC1.O=[N+:8]([O-])[c:7]1[cH:6][cH:5][cH:4][c:3]([CH:2]([CH3:1])[n:10]2[c:11](=[O:12])[o:13][c:14]3[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]23)[cH:9]1.[Ni] | [CH3:1][CH:2]([c:3]1[cH:4][cH:5][cH:6][c:7]([NH2:8])[cH:9]1)[n:10]1[c:11](=[O:12])[o:13][c:14]2[cH:15][c:16]([F:17])[c:18]([F:19])[cH:20][c:21]12 | ([#7;a:8]-[C:7]-[c:6]1:[c:5]:[c:4]:[c:3]:[c:2](-[NH2;D1;+0:1]):[c:9]:1)>>(O=[N+;H0;D3:1](-[O-])-[c:2]1:[c:3]:[c:4]:[c:5]:[c:6](-[C:7]-[#7;a:8]):[c:9]:1) | 8ae831c82dc079dbdfba5f54795c649cace852fd2bea6506c3577b69 | 1 | 1 | C1CCOC1.[Ni] | 71 |
128,596 | 470,980 | 796,689 | [CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N+:19]([O-])=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2]>CO.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[NH2:19])[CH2:8][CH2:7]1)=[O:5])[CH3:2] | null | US07244744B2_0146 | 2,007 | CO.O=[N+:17]([O-])[c:16]1[c:11]([NH:10][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:19][CH2:18]2)[cH:12][cH:13][cH:14][cH:15]1.[Pd]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[CH2:18][CH2:19]1 | 0.958122 | CCOC(=O)N1CCC(Nc2ccccc2[N+](=O)[O-])CC1.CO.[Pd]>>CCOC(=O)N1CCC(Nc2ccccc2N)CC1 | CCOC(=O)N1CCC(Nc2ccccc2[N+](=O)[O-])CC1.CO.[Pd]>>CCOC(=O)N1CCC(Nc2ccccc2N)CC1 | US07244744B2_0146grants | f6fbed033fc2dea2bfa3de1ace7b20f5839a2657e14af5b460a2b62e | CO.O=[N+:17]([O-])[c:16]1[c:11]([NH:10][CH:9]2[CH2:8][CH2:7][N:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH2:19][CH2:18]2)[cH:12][cH:13][cH:14][cH:15]1.[Pd] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[N:6]1[CH2:7][CH2:8][CH:9]([NH:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[NH2:17])[CH2:18][CH2:19]1 | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | CO.[Pd] | 1 |
213,070 | 718,664 | 1,183,305 | [F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4](O)=[O:5].C(Cl)(=O)C(Cl)=O.Cl.[CH3:18][NH:19][O:20][CH3:21].C(N(CC)C(C)C)(C)C>CN(C=O)C.C(Cl)Cl.CCOCC>[F:1][C:2]([F:10])([F:9])[C:3]([CH3:8])([CH3:7])[C:4]([N:19]([O:20][CH3:21])[CH3:18])=[O:5] | |f:2.3| | US08163901B2_0504 | 2,012 | CCN(C(C)C)C(C)C.CCOCC.CN(C)C=O.Cl.ClCCl.O=C(Cl)C(=O)Cl.O[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[C:10]([F:11])([F:12])[F:13].[CH3:1][O:2][NH:3][CH3:4]>>[CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[C:10]([F:11])([F:12])[F:13] | 0.232258 | CC(C)(C(=O)O)C(F)(F)F.CCN(C(C)C)C(C)C.CCOCC.CN(C)C=O.CNOC~Cl.ClCCl.O=C(Cl)C(=O)Cl>>CON(C)C(=O)C(C)(C)C(F)(F)F | CC(C)(C(=O)O)C(F)(F)F.CCN(C(C)C)C(C)C.CCOCC.CN(C)C=O.CNOC.Cl.ClCCl.O=C(Cl)C(=O)Cl>>CON(C)C(=O)C(C)(C)C(F)(F)F | US08163901B2_0504grants | 7b3a788345dd449e339bdea220fb1cf311cc366715a90acd1cd74874 | CCN(C(C)C)C(C)C.CCOCC.CN(C)C=O.Cl.ClCCl.O=C(Cl)C(=O)Cl.O[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[C:10]([F:11])([F:12])[F:13].[CH3:1][O:2][NH:3][CH3:4] | [CH3:1][O:2][N:3]([CH3:4])[C:5](=[O:6])[C:7]([CH3:8])([CH3:9])[C:10]([F:11])([F:12])[F:13] | ([#8:4]-[N;H0;D3;+0:5](-[C;D1;H3:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([#8:4]-[NH;D2;+0:5]-[C;D1;H3:6]) | e12e17c16fdd82cb71a098517c68119425dd3668f93c08def7cb5247 | 1 | 1 | CCN(C(C)C)C(C)C.CCOCC.CN(C)C=O.Cl.ClCCl.O=C(Cl)C(=O)Cl | 54 |
152,754 | 544,904 | 912,444 | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:7]=1 | null | US07566735B2_1106 | 2,009 | O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | 0.798105 | C1CCNC1.O=C(O)CCc1ccc(Br)cc1>>O=C(CCc1ccc(Br)cc1)N1CCCC1 | C1CCNC1.O=C(O)CCc1ccc(Br)cc1>>O=C(CCc1ccc(Br)cc1)N1CCCC1 | US07566735B2_1106grants | 1f11873af8ec3ed3cae19797f40e1cf064cb0e2e1fecdc7d6a436031 | O[C:2](=[O:1])[CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1.[NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | [O:1]=[C:2]([CH2:3][CH2:4][c:5]1[cH:6][cH:7][c:8]([Br:9])[cH:10][cH:11]1)[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | null | 146 |
433,639 | 1,863,441 | null | [Br:1][C:2]1[N:7]=[C:6]([C@:8]2([CH3:29])[CH2:13][S@:12](=[N:15][CH2:16][CH2:17][OH:18])(=[O:14])[C:11]([CH3:20])([CH3:19])[C:10]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[N:9]2)[C:5]([F:30])=[C:4]([Si:31]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:32][CH3:33])[CH:3]=1.[S:38](Cl)([C:41]1[CH:47]=[CH:46][C:44]([CH3:45])=[CH:43][CH:42]=1)(=[O:40])=[O:39].C(N(CC)CC)C.O>ClCCl.CN(C)C1C=CN=CC=1>[CH3:45][C:44]1[CH:46]=[CH:47][C:41]([S:38]([O:18][CH2:17][CH2:16][N:15]=[S@@:12]2(=[O:14])[C:11]([CH3:19])([CH3:20])[C:10]([NH:21][C:22]([O:23][C:24]([CH3:27])([CH3:25])[CH3:26])=[O:28])=[N:9][C@@:8]([C:6]3[C:5]([F:30])=[C:4]([Si:31]([CH2:36][CH3:37])([CH2:34][CH3:35])[CH2:32][CH3:33])[CH:3]=[C:2]([Br:1])[N:7]=3)([CH3:29])[CH2:13]2)(=[O:40])=[O:39])=[CH:42][CH:43]=1 | null | US20160102105A1_0634 | 2,016 | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.Cl[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([CH3:30])[cH:31][cH:32]1.O.[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[c:8]1[cH:9][c:10]([Br:11])[n:12][c:13]([C@:14]2([CH3:15])[CH2:16][S@@:17](=[O:18])(=[N:19][CH2:20][CH2:21][OH:22])[C:33]([CH3:34])([CH3:35])[C:36]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[N:45]2)[c:46]1[F:47]>>[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[c:8]1[cH:9][c:10]([Br:11])[n:12][c:13]([C@:14]2([CH3:15])[CH2:16][S@@:17](=[O:18])(=[N:19][CH2:20][CH2:21][O:22][S:23](=[O:24])(=[O:25])[c:26]3[cH:27][cH:28][c:29]([CH3:30])[cH:31][cH:32]3)[C:33]([CH3:34])([CH3:35])[C:36]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[N:45]2)[c:46]1[F:47] | 0.07885 | CCN(CC)CC.CC[Si](CC)(CC)c1cc(Br)nc([C@]2(C)C[S@@](=O)(=NCCO)C(C)(C)C(NC(=O)OC(C)(C)C)=N2)c1F.CN(C)c1ccncc1.Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.O>>CC[Si](CC)(CC)c1cc(Br)nc([C@]2(C)C[S@@](=O)(=NCCOS(=O)(=O)c3ccc(C)cc3)C(C)(C)C(NC(=O)OC(C)(C)C)=N2)c1F | CCN(CC)CC.CC[Si](CC)(CC)c1cc(Br)nc([C@]2(C)C[S@@](=O)(=NCCO)C(C)(C)C(NC(=O)OC(C)(C)C)=N2)c1F.CN(C)c1ccncc1.Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.O>>CC[Si](CC)(CC)c1cc(Br)nc([C@]2(C)C[S@@](=O)(=NCCOS(=O)(=O)c3ccc(C)cc3)C(C)(C)C(NC(=O)OC(C)(C)C)=N2)c1F | US20160102105A1_0634apps | 0d792ccba2fe8cd2429176b4095d181113cbc1c98c316843379744c9 | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.Cl[S:23](=[O:24])(=[O:25])[c:26]1[cH:27][cH:28][c:29]([CH3:30])[cH:31][cH:32]1.O.[CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[c:8]1[cH:9][c:10]([Br:11])[n:12][c:13]([C@:14]2([CH3:15])[CH2:16][S@@:17](=[O:18])(=[N:19][CH2:20][CH2:21][OH:22])[C:33]([CH3:34])([CH3:35])[C:36]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[N:45]2)[c:46]1[F:47] | [CH3:1][CH2:2][Si:3]([CH2:4][CH3:5])([CH2:6][CH3:7])[c:8]1[cH:9][c:10]([Br:11])[n:12][c:13]([C@:14]2([CH3:15])[CH2:16][S@@:17](=[O:18])(=[N:19][CH2:20][CH2:21][O:22][S:23](=[O:24])(=[O:25])[c:26]3[cH:27][cH:28][c:29]([CH3:30])[cH:31][cH:32]3)[C:33]([CH3:34])([CH3:35])[C:36]([NH:37][C:38](=[O:39])[O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[N:45]2)[c:46]1[F:47] | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[OH;D1;+0:6]) | 2a680215c1c69f116045ff1696194ac3ca890d5406b0abc3856bedc8 | 1 | 1 | CCN(CC)CC.CN(C)c1ccncc1.ClCCl.O | 197 |
219,563 | 737,959 | 1,215,557 | [C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][C:9]([CH2:18][CH2:19][CH:20]=O)=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1.CCN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[CH3:22][C:23]1[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:24]=1[N:30]1[CH2:31][CH2:32][N:33]([CH2:20][CH2:19][CH2:18][C:9]2[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH2:34][CH2:35]1 | |f:3.4| | US08236806B2_0264 | 2,012 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.O=[CH:11][CH2:12][CH2:13][c:14]1[cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[n:30]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:31][CH2:32]2)[c:33]1[CH3:34].[Na+]>>[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]3[cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[n:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[n:30]3)[CH2:31][CH2:32]2)[c:33]1[CH3:34] | 0.782383 | CC(=O)O[BH-](OC(C)=O)OC(C)=O~[Na+].CCN(C(C)C)C(C)C.Cc1cccc(N2CCNCC2)c1C.O=CCCc1cc(-c2ccccc2)n(-c2ccccc2)n1>>Cc1cccc(N2CCN(CCCc3cc(-c4ccccc4)n(-c4ccccc4)n3)CC2)c1C | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.Cc1cccc(N2CCNCC2)c1C.O=CCCc1cc(-c2ccccc2)n(-c2ccccc2)n1.[Na+]>>Cc1cccc(N2CCN(CCCc3cc(-c4ccccc4)n(-c4ccccc4)n3)CC2)c1C | US08236806B2_0264grants | 807ba2d6d9b7bf9c7fe805b2a7a42e6dac2a5de23e0e7421540a5e53 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.O=[CH:11][CH2:12][CH2:13][c:14]1[cH:15][c:16](-[c:17]2[cH:18][cH:19][cH:20][cH:21][cH:22]2)[n:23](-[c:24]2[cH:25][cH:26][cH:27][cH:28][cH:29]2)[n:30]1.[CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][NH:10][CH2:31][CH2:32]2)[c:33]1[CH3:34].[Na+] | [CH3:1][c:2]1[cH:3][cH:4][cH:5][c:6]([N:7]2[CH2:8][CH2:9][N:10]([CH2:11][CH2:12][CH2:13][c:14]3[cH:15][c:16](-[c:17]4[cH:18][cH:19][cH:20][cH:21][cH:22]4)[n:23](-[c:24]4[cH:25][cH:26][cH:27][cH:28][cH:29]4)[n:30]3)[CH2:31][CH2:32]2)[c:33]1[CH3:34] | ([C:2]-[CH2;D2;+0:1]-[N;H0;D3;+0:4](-[C:3])-[C:5])>>(O=[CH;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 1eecabe0173fa39f206a365ccea98e2b763ff157e33c23433b777de4 | 0.5 | 2 | CC(=O)O[BH-](OC(C)=O)OC(C)=O.CCN(C(C)C)C(C)C.[Na+] | 484 |
425,512 | 1,808,459 | null | Cl.[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C:17]([NH2:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:10])(=[O:9])[N:8]=1.[CH3:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][N:30]=1)[C:25](O)=[O:26]>>[NH2:2][C:3]1[C:4]2[C:14]([O:15][CH2:16][C:17]([NH:20][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][N:30]=[C:22]([CH3:21])[CH:23]=3)([CH3:18])[CH3:19])=[CH:13][CH:12]=[CH:11][C:5]=2[NH:6][S:7](=[O:10])(=[O:9])[N:8]=1 | |f:0.1| | US20150376176A1_0147 | 2,015 | Cl.O[C:5]([c:4]1[cH:3][c:2]([CH3:1])[n:28][cH:27][cH:26]1)=[O:6].[NH2:7][C:8]([CH3:9])([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[C:19]([NH2:20])=[N:21][S:22](=[O:23])(=[O:24])[NH:25]2>>[CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[NH:7][C:8]([CH3:9])([CH3:10])[CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19]([NH2:20])=[N:21][S:22](=[O:23])(=[O:24])[NH:25]3)[cH:26][cH:27][n:28]1 | 0.481309 | CC(C)(N)COc1cccc2c1C(N)=NS(=O)(=O)N2~Cl.Cc1cc(C(=O)O)ccn1>>Cc1cc(C(=O)NC(C)(C)COc2cccc3c2C(N)=NS(=O)(=O)N3)ccn1 | CC(C)(N)COc1cccc2c1C(N)=NS(=O)(=O)N2.Cc1cc(C(=O)O)ccn1.Cl>>Cc1cc(C(=O)NC(C)(C)COc2cccc3c2C(N)=NS(=O)(=O)N3)ccn1 | US20150376176A1_0147apps | 6fb6cb7caf6e2d21993eecade3bf666cff76f5180ad0063049718def | Cl.O[C:5]([c:4]1[cH:3][c:2]([CH3:1])[n:28][cH:27][cH:26]1)=[O:6].[NH2:7][C:8]([CH3:9])([CH3:10])[CH2:11][O:12][c:13]1[cH:14][cH:15][cH:16][c:17]2[c:18]1[C:19]([NH2:20])=[N:21][S:22](=[O:23])(=[O:24])[NH:25]2 | [CH3:1][c:2]1[cH:3][c:4]([C:5](=[O:6])[NH:7][C:8]([CH3:9])([CH3:10])[CH2:11][O:12][c:13]2[cH:14][cH:15][cH:16][c:17]3[c:18]2[C:19]([NH2:20])=[N:21][S:22](=[O:23])(=[O:24])[NH:25]3)[cH:26][cH:27][n:28]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | Cl | 334 |
87,174 | 347,118 | 592,035 | N1C=CC=CC=1.Cl[C:8]([O:10][CH3:11])=[O:9].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:41]2[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=2)[N:20]2[CH2:23][C:22](=[CH:24][S:25]([CH2:28][C:29]3[CH:30]=[C:31]([N:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)[CH:32]=[CH:33][CH:34]=3)(=[O:27])=[O:26])[CH2:21]2)=[CH:15][CH:14]=1>C(OCC)(=O)C.O>[CH3:11][O:10][C:8]([N:38]1[CH2:39][CH2:40][N:35]([C:31]2[CH:32]=[CH:33][CH:34]=[C:29]([CH2:28][S:25]([CH:24]=[C:22]3[CH2:21][N:20]([CH:19]([C:16]4[CH:15]=[CH:14][C:13]([Cl:12])=[CH:18][CH:17]=4)[C:41]4[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][CH:42]=4)[CH2:23]3)(=[O:26])=[O:27])[CH:30]=2)[CH2:36][CH2:37]1)=[O:9] | null | US06518264B2_ | 2,003 | CCOC(C)=O.Cl[C:3]([O:2][CH3:1])=[O:4].O.[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([CH2:14][S:15](=[O:16])(=[O:17])[CH:18]=[C:19]3[CH2:20][N:21]([CH:22]([c:23]4[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]4)[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37]3)[cH:38]2)[CH2:39][CH2:40]1.c1ccncc1>>[CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([CH2:14][S:15](=[O:16])(=[O:17])[CH:18]=[C:19]3[CH2:20][N:21]([CH:22]([c:23]4[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]4)[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37]3)[cH:38]2)[CH2:39][CH2:40]1 | 0.401107 | CCOC(C)=O.COC(=O)Cl.O.O=S(=O)(C=C1CN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1)Cc1cccc(N2CCNCC2)c1.c1ccncc1>>COC(=O)N1CCN(c2cccc(CS(=O)(=O)C=C3CN(C(c4ccc(Cl)cc4)c4ccc(Cl)cc4)C3)c2)CC1 | CCOC(C)=O.COC(=O)Cl.O.O=S(=O)(C=C1CN(C(c2ccc(Cl)cc2)c2ccc(Cl)cc2)C1)Cc1cccc(N2CCNCC2)c1.c1ccncc1>>COC(=O)N1CCN(c2cccc(CS(=O)(=O)C=C3CN(C(c4ccc(Cl)cc4)c4ccc(Cl)cc4)C3)c2)CC1 | US06518264B2_grants | a7fd666986a84bb579081e033cfe37fb329329165a6e8bdb4e166ee7 | CCOC(C)=O.Cl[C:3]([O:2][CH3:1])=[O:4].O.[NH:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([CH2:14][S:15](=[O:16])(=[O:17])[CH:18]=[C:19]3[CH2:20][N:21]([CH:22]([c:23]4[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]4)[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37]3)[cH:38]2)[CH2:39][CH2:40]1.c1ccncc1 | [CH3:1][O:2][C:3](=[O:4])[N:5]1[CH2:6][CH2:7][N:8]([c:9]2[cH:10][cH:11][cH:12][c:13]([CH2:14][S:15](=[O:16])(=[O:17])[CH:18]=[C:19]3[CH2:20][N:21]([CH:22]([c:23]4[cH:24][cH:25][c:26]([Cl:27])[cH:28][cH:29]4)[c:30]4[cH:31][cH:32][c:33]([Cl:34])[cH:35][cH:36]4)[CH2:37]3)[cH:38]2)[CH2:39][CH2:40]1 | ([#8:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[N;H0;D3;+0:5](-[C:4])-[C:6])>>(Cl-[C;H0;D3;+0:1](-[#8:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | a8ad6d981577e38ffa105f9cec0abb9f8b4d3de801fd8006168b839b | 1 | 1 | CCOC(C)=O.O.c1ccncc1 | 219 |
26,690 | 124,639 | 201,588 | [Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2.[N+:19]([O-])([OH:21])=[O:20]>S(=O)(=O)(O)O>[Cl:1][C:2]1[N:3]([C:11]2[CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[C:14]([F:17])=[CH:13][C:12]=2[F:18])[N:4]=[C:5]2[C:10]=1[CH2:9][CH2:8][CH2:7][CH2:6]2 | null | US04877444_ | 1,989 | O=S(=O)(O)O.O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6](-[n:7]2[n:8][c:9]3[c:10]([c:11]2[Cl:12])[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]([F:18])[cH:19][c:20]1[F:21]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[n:7]2[n:8][c:9]3[c:10]([c:11]2[Cl:12])[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]([F:18])[cH:19][c:20]1[F:21] | 0.777144 | Fc1ccc(-n2nc3c(c2Cl)CCCC3)c(F)c1.O=S(=O)(O)O.O=[N+]([O-])O>>O=[N+]([O-])c1cc(-n2nc3c(c2Cl)CCCC3)c(F)cc1F | Fc1ccc(-n2nc3c(c2Cl)CCCC3)c(F)c1.O=S(=O)(O)O.O=[N+]([O-])O>>O=[N+]([O-])c1cc(-n2nc3c(c2Cl)CCCC3)c(F)cc1F | US04877444_grants | ff83ef5f7fca15ca712afe22bb9903428bf0801eebf3d58d86b21ffa | O=S(=O)(O)O.O[N+:2](=[O:1])[O-:3].[cH:4]1[cH:5][c:6](-[n:7]2[n:8][c:9]3[c:10]([c:11]2[Cl:12])[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]([F:18])[cH:19][c:20]1[F:21] | [O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[n:7]2[n:8][c:9]3[c:10]([c:11]2[Cl:12])[CH2:13][CH2:14][CH2:15][CH2:16]3)[c:17]([F:18])[cH:19][c:20]1[F:21] | ([O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:5](:[c:4]):[c:6])>>(O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]).([c:4]:[cH;D2;+0:5]:[c:6]) | c25d51e5af868cef93abbb502e1d42ba1564ccc8abe5e0e442b85ea3 | 1 | 1 | O=S(=O)(O)O | 21 |
192,298 | 662,086 | 1,095,636 | [Cl:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=2)[CH:7]=1.[CH3:14][N:15]([CH3:29])[C:16]([C:18]1[C:19]2[CH2:20][CH2:21][NH:22][CH:23]([CH3:28])[C:24]=2[CH:25]=[CH:26][CH:27]=1)=[O:17]>>[CH3:14][N:15]([CH3:29])[C:16]([C:18]1[C:19]2[CH2:20][CH2:21][N:22]([C:11]([C:9]3[CH:10]=[C:5]4[N:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]4[N:8]=3)=[O:13])[CH:23]([CH3:28])[C:24]=2[CH:25]=[CH:26][CH:27]=1)=[O:17] | null | US07985753B2_1590 | 2,011 | O[C:17](=[O:18])[c:19]1[cH:20][c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2[n:28]1.[CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH3:11])[CH3:12])[c:13]2[CH2:14][CH2:15][NH:16]1>>[CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH3:11])[CH3:12])[c:13]2[CH2:14][CH2:15][N:16]1[C:17](=[O:18])[c:19]1[cH:20][c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2[n:28]1 | 0.619205 | CC1NCCc2c(C(=O)N(C)C)cccc21.O=C(O)c1cc2ncc(Cl)cn2n1>>CC1c2cccc(C(=O)N(C)C)c2CCN1C(=O)c1cc2ncc(Cl)cn2n1 | CC1NCCc2c(C(=O)N(C)C)cccc21.O=C(O)c1cc2ncc(Cl)cn2n1>>CC1c2cccc(C(=O)N(C)C)c2CCN1C(=O)c1cc2ncc(Cl)cn2n1 | US07985753B2_1590grants | 18b85194094741640d9fba1e10e818e6d899367f2d1636b5f0aa03d0 | O[C:17](=[O:18])[c:19]1[cH:20][c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2[n:28]1.[CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH3:11])[CH3:12])[c:13]2[CH2:14][CH2:15][NH:16]1 | [CH3:1][CH:2]1[c:3]2[cH:4][cH:5][cH:6][c:7]([C:8](=[O:9])[N:10]([CH3:11])[CH3:12])[c:13]2[CH2:14][CH2:15][N:16]1[C:17](=[O:18])[c:19]1[cH:20][c:21]2[n:22][cH:23][c:24]([Cl:25])[cH:26][n:27]2[n:28]1 | ([#7;a:5]:[#7;a:4]:[c:3]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[N;H0;D3;+0:7](-[C:6])-[C:8]-[c:9]1:[c:10]:[c:11]:[c:12]:[c:13]:[c:14]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]:[#7;a:4]:[#7;a:5]).([C:6]-[NH;D2;+0:7]-[C:8]-[c:9]1:[c:10]:[c:11]:[c:12]:[c:13]:[c:14]:1) | bdbe3487d827d9915cac471e6ca041ff711379d99f4fb6a4fd9b04ff | 1 | 1 | null | 952 |
135,655 | 492,198 | 829,214 | [CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:14])[CH2:12][OH:13])=[CH:5][CH:4]=1.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>N1C=CC=CC=1>[C:17]([O:13][CH2:12][C@@H:11]([OH:14])[CH2:10][CH2:9][O:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1 | null | US07348148B2_0262 | 2,008 | Cl[C:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][OH:14])[cH:34][cH:35]1.c1ccncc1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][O:14][C:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1 | 0.209631 | COc1ccc(COCC[C@H](O)CO)cc1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1ccncc1>>COc1ccc(COCC[C@H](O)COC(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | COc1ccc(COCC[C@H](O)CO)cc1.ClC(c1ccccc1)(c1ccccc1)c1ccccc1.c1ccncc1>>COc1ccc(COCC[C@H](O)COC(c2ccccc2)(c2ccccc2)c2ccccc2)cc1 | US07348148B2_0262grants | 547c4c3edb77aad10e34a68ed3c9e311a45ddd79b8988167f7bce1bb | Cl[C:15]([c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1)([c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1)[c:28]1[cH:29][cH:30][cH:31][cH:32][cH:33]1.[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][OH:14])[cH:34][cH:35]1.c1ccncc1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][CH2:9][CH2:10][C@H:11]([OH:12])[CH2:13][O:14][C:15]([c:16]2[cH:17][cH:18][cH:19][cH:20][cH:21]2)([c:22]2[cH:23][cH:24][cH:25][cH:26][cH:27]2)[c:28]2[cH:29][cH:30][cH:31][cH:32][cH:33]2)[cH:34][cH:35]1 | ([C:5]-[O;H0;D2;+0:6]-[C;H0;D4;+0:1](-[c:2])(-[c:3])-[c:4])>>(Cl-[C;H0;D4;+0:1](-[c:2])(-[c:3])-[c:4]).([C:5]-[OH;D1;+0:6]) | 717bf7de7e9d2a619323767a974ed3e69ddbe66a0833178fec1b971a | 1 | 1 | c1ccncc1 | 250 |
379,699 | 929,176 | null | [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:21]Br)([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O.ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=2)([CH2:21][O:37][C:33]2[CH:34]=[CH:35][CH:36]=[C:31]([O:30][CH3:29])[CH:32]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:4])[CH3:3] | |f:1.2.3| | US20100210617A1_1323 | 2,010 | Br[CH2:9][C:10]1([c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1.CN(C)C=O.ClCCl.O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:30]1.[Cs+].[Cs+]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH2:9][C:10]2([c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:30]1 | 0.349844 | CC(C)(C)OC(=O)N1CCC(CBr)(c2ccc(Br)cc2)CC1.CN(C)C=O.COc1cccc(O)c1.ClCCl.O=C([O-])[O-]~[Cs+]~[Cs+]>>COc1cccc(OCC2(c3ccc(Br)cc3)CCN(C(=O)OC(C)(C)C)CC2)c1 | CC(C)(C)OC(=O)N1CCC(CBr)(c2ccc(Br)cc2)CC1.CN(C)C=O.COc1cccc(O)c1.ClCCl.O=C([O-])[O-].[Cs+].[Cs+]>>COc1cccc(OCC2(c3ccc(Br)cc3)CCN(C(=O)OC(C)(C)C)CC2)c1 | US20100210617A1_1323apps | 891f9109d06bf00a24743329e7c9049eed70265979f3e0eca8cc6477 | Br[CH2:9][C:10]1([c:11]2[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]2)[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]1.CN(C)C=O.ClCCl.O=C([O-])[O-].[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([OH:8])[cH:30]1.[Cs+].[Cs+] | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([O:8][CH2:9][C:10]2([c:11]3[cH:12][cH:13][c:14]([Br:15])[cH:16][cH:17]3)[CH2:18][CH2:19][N:20]([C:21](=[O:22])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28][CH2:29]2)[cH:30]1 | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 77cefa6f7285e1367b00e291ad0c233a215688d867a7713380b3385d | 1 | 1 | CN(C)C=O.ClCCl.O=C([O-])[O-].[Cs+].[Cs+] | 75 |
168,337 | 591,386 | 981,324 | [Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12] | null | US07723332B2_0203 | 2,010 | ClCCl.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11]1.[NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1>>[O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11]1)[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | 0.762755 | C1CCNC1.ClCCl.O=S(=O)(Cl)c1ccc(Br)c(F)c1>>O=S(=O)(c1ccc(Br)c(F)c1)N1CCCC1 | C1CCNC1.ClCCl.O=S(=O)(Cl)c1ccc(Br)c(F)c1>>O=S(=O)(c1ccc(Br)c(F)c1)N1CCCC1 | US07723332B2_0203grants | 279e0d33b6a5394d68abe0d8d63c8f6a725b399dd3944d847dc5a496 | ClCCl.Cl[S:2](=[O:1])(=[O:3])[c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11]1.[NH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | [O:1]=[S:2](=[O:3])([c:4]1[cH:5][cH:6][c:7]([Br:8])[c:9]([F:10])[cH:11]1)[N:12]1[CH2:13][CH2:14][CH2:15][CH2:16]1 | ([C:5]-[N;H0;D3;+0:6](-[C:7])-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 1c3a913f221c79d5ab4e40f13ae7431f2711f9942a72ad3fc8bf5434 | 1 | 1 | ClCCl | 99 |
75,928 | 309,669 | 525,469 | Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[CH2:9][S:8][CH2:7]1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+].[Br-]>[Na+].[I-].CO.C(Cl)(Cl)Cl>[F:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[CH2:9][S:8][CH2:7]3)[CH2:21][CH2:20]2)=[CH:17][CH:18]=1 | |f:2.3.4,6.7,8.9| | US06284775B1_ | 2,001 | Br[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:2](=[O:1])[CH2:3][S:4][CH2:5]1.CO.ClC(Cl)Cl.O=C([O-])[O-].[Br-].[I-].[K+].[K+].[NH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1.[Na+]>>[O:1]=[C:2]1[CH2:3][S:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1 | 0.78796 | CO~ClC(Cl)Cl.Fc1ccc(N2CCNCC2)cc1.O=C([O-])[O-]~[K+]~[K+].O=C1CSCN1CCCCBr.[Br-].[I-]~[Na+]>>O=C1CSCN1CCCCN1CCN(c2ccc(F)cc2)CC1 | CO.ClC(Cl)Cl.Fc1ccc(N2CCNCC2)cc1.O=C([O-])[O-].O=C1CSCN1CCCCBr.[Br-].[I-].[K+].[K+].[Na+]>>O=C1CSCN1CCCCN1CCN(c2ccc(F)cc2)CC1 | US06284775B1_grants | 001970d338e7ccf86ac4651fb6a6ba3dd960ced143b7ca20a8031368 | Br[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:2](=[O:1])[CH2:3][S:4][CH2:5]1.CO.ClC(Cl)Cl.O=C([O-])[O-].[Br-].[I-].[K+].[K+].[NH:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1.[Na+] | [O:1]=[C:2]1[CH2:3][S:4][CH2:5][N:6]1[CH2:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:12][CH2:13][N:14]([c:15]2[cH:16][cH:17][c:18]([F:19])[cH:20][cH:21]2)[CH2:22][CH2:23]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(Br-[CH2;D2;+0:1]-[C:2]).([C:3]-[NH;D2;+0:4]-[C:5]) | 53994dd2d8bb14288cdfb7c2951155e80ca49e2c98f7d531177a38b3 | 0.333333 | 3 | CO.ClC(Cl)Cl.O=C([O-])[O-].[Br-].[I-].[K+].[K+].[Na+] | 73 |
310,352 | 1,009,245 | 1,708,082 | Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[OH:19])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH2:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)[CH3:12] | |f:2.3.4| | US09216967B2_0592 | 2,015 | CN(C)C=O.Cl[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1.O=C([O-])[O-].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].[K+].[K+]>>[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1 | 0.965598 | CCc1ccccc1O.CN(C)C=O.O=C([O-])[O-]~[K+]~[K+].O=[N+]([O-])c1ccc(Cl)nc1>>CCc1ccccc1Oc1ccc([N+](=O)[O-])cn1 | CCc1ccccc1O.CN(C)C=O.O=C([O-])[O-].O=[N+]([O-])c1ccc(Cl)nc1.[K+].[K+]>>CCc1ccccc1Oc1ccc([N+](=O)[O-])cn1 | US09216967B2_0592grants | d3030b8f0c1bfb16751f9a52600d6602f5945a0d273be0c2bbdb98c2 | CN(C)C=O.Cl[c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1.O=C([O-])[O-].[CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[OH:9].[K+].[K+] | [CH3:1][CH2:2][c:3]1[cH:4][cH:5][cH:6][cH:7][c:8]1[O:9][c:10]1[cH:11][cH:12][c:13]([N+:14](=[O:15])[O-:16])[cH:17][n:18]1 | ([#7;a:2]:[c;H0;D3;+0:1](:[c:3])-[O;H0;D2;+0:4]-[c:5])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]).([OH;D1;+0:4]-[c:5]) | b2089f895c9c3865a4c9e6f4846c2664b59c6ecfe2c6720268cccbc1 | 1 | 1 | CN(C)C=O.O=C([O-])[O-].[K+].[K+] | 516 |
225,606 | 756,397 | 1,246,367 | [Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15](OC)=[O:16])[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[K+]>C(OCC)C>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][OH:16])[CH2:13][CH2:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2] | |f:1.2.3.4.5.6,8.9| | US08304412B2_0348 | 2,012 | CCOCC.CO[C:13]([CH:12]1[CH2:11][CH2:10][CH:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:16][CH2:15]1)=[O:14].O.[Al+3].[H-].[H-].[H-].[H-].[K+].[Li+].[OH-]>>[CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:13][OH:14])[CH2:15][CH2:16]1 | 0.295123 | CCOCC.COC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CC1.O.[Al+3]~[H-]~[H-]~[H-]~[H-]~[Li+].[K+]~[OH-]>>CC(C)(C)[Si](C)(C)OC1CCC(CO)CC1 | CCOCC.COC(=O)C1CCC(O[Si](C)(C)C(C)(C)C)CC1.O.[Al+3].[H-].[H-].[H-].[H-].[K+].[Li+].[OH-]>>CC(C)(C)[Si](C)(C)OC1CCC(CO)CC1 | US08304412B2_0348grants | c961fec46d4df695a6a2d40907b29eeb070bcc89ebe0f20e589e4e3c | CCOCC.CO[C:13]([CH:12]1[CH2:11][CH2:10][CH:9]([O:8][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:6])[CH3:7])[CH2:16][CH2:15]1)=[O:14].O.[Al+3].[H-].[H-].[H-].[H-].[K+].[Li+].[OH-] | [CH3:1][C:2]([CH3:3])([CH3:4])[Si:5]([CH3:6])([CH3:7])[O:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:13][OH:14])[CH2:15][CH2:16]1 | ([C:2]-[CH2;D2;+0:1]-[OH;D1;+0:3])>>(C-O-[C;H0;D3;+0:1](-[C:2])=[O;H0;D1;+0:3]) | ace077327b65885e2493775e77cea5434d2da2918de8308af58629a6 | 1 | 1 | CCOCC.O.[Al+3].[H-].[H-].[H-].[H-].[K+].[Li+].[OH-] | 343 |
140,601 | 508,000 | 852,383 | [Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:16]O>CCOCC>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([O:6][CH3:16])=[O:5] | null | US07417045B2_0450 | 2,008 | CCOCC.O=S(Cl)Cl.O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Cl:12]>>[CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Cl:12] | 0.740855 | CCOCC.CO.O=C(O)c1cc(Cl)cnc1Cl.O=S(Cl)Cl>>COC(=O)c1cc(Cl)cnc1Cl | CCOCC.CO.O=C(O)c1cc(Cl)cnc1Cl.O=S(Cl)Cl>>COC(=O)c1cc(Cl)cnc1Cl | US07417045B2_0450grants | 23d09d7d43e87279784e222a46809ca536ed997ae75d5c7d5250c584 | CCOCC.O=S(Cl)Cl.O[CH3:1].[OH:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Cl:12] | [CH3:1][O:2][C:3](=[O:4])[c:5]1[cH:6][c:7]([Cl:8])[cH:9][n:10][c:11]1[Cl:12] | ([CH3;D1;+0:1]-[O;H0;D2;+0:4]-[C:3]=[O;D1;H0:2])>>(O-[CH3;D1;+0:1]).([O;D1;H0:2]=[C:3]-[OH;D1;+0:4]) | e189425e090fce77131c907ebf1468461240dd27d4457a40d701e43e | 1 | 1 | CCOCC.O=S(Cl)Cl | 195 |
48,657 | 211,775 | 342,460 | [H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[NH:13][CH3:14].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CN(C)C=O>[Cl:19][CH2:18][CH2:17][CH2:16][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:12])[CH3:11])=[CH:6][C:5]=1[NH:13][CH3:14] | |f:0.1| | US05550130_ | 1,996 | Br[CH2:13][CH2:14][CH2:15][Cl:16].CN(C)C=O.[CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[OH:12].[H-].[Na+]>>[CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][Cl:16] | 0.994161 | CN(C)C=O.CNc1cc(C(C)=O)ccc1O.ClCCCBr.[H-]~[Na+]>>CNc1cc(C(C)=O)ccc1OCCCCl | CN(C)C=O.CNc1cc(C(C)=O)ccc1O.ClCCCBr.[H-].[Na+]>>CNc1cc(C(C)=O)ccc1OCCCCl | US05550130_grants | 4ae74e153b0c304919886776ee4c2ef519923ee7b68681b351e337ac | Br[CH2:13][CH2:14][CH2:15][Cl:16].CN(C)C=O.[CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[OH:12].[H-].[Na+] | [CH3:1][NH:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][cH:10][c:11]1[O:12][CH2:13][CH2:14][CH2:15][Cl:16] | ([C:2]-[CH2;D2;+0:1]-[O;H0;D2;+0:3]-[c:4])>>(Br-[CH2;D2;+0:1]-[C:2]).([OH;D1;+0:3]-[c:4]) | 77cefa6f7285e1367b00e291ad0c233a215688d867a7713380b3385d | 1 | 1 | CN(C)C=O.[H-].[Na+] | 75 |
43,153 | 190,235 | 306,329 | [C:1]([CH:5]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([CH3:25])=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]=[C:16]2[CH2:26][CH3:27])=[CH:9][C:8]=1[CH3:28])([O:3]C)=[O:2].[OH-].[Na+].Cl>CO>[C:1]([CH:5]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[CH:30]=1)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH2:14][N:15]2[C:19]3=[N:20][C:21]([CH3:25])=[CH:22][C:23]([CH3:24])=[C:18]3[N:17]=[C:16]2[CH2:26][CH3:27])=[CH:9][C:8]=1[CH3:28])([OH:3])=[O:2] | |f:1.2| | US05374638_ | 1,994 | CO.C[O:24][C:22]([CH:21]([O:20][c:19]1[c:17]([CH3:18])[cH:16][c:15]([CH2:14][n:13]2[c:3]([CH2:2][CH3:1])[n:4][c:5]3[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[n:11][c:12]32)[cH:34][c:32]1[CH3:33])[c:25]1[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)=[O:23].Cl.[Na+].[OH-]>>[CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[n:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][c:17]([CH3:18])[c:19]([O:20][CH:21]([C:22](=[O:23])[OH:24])[c:25]2[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[c:32]([CH3:33])[cH:34]1 | 0.921064 | CCc1nc2c(C)cc(C)nc2n1Cc1cc(C)c(OC(C(=O)OC)c2cccc(Cl)c2)c(C)c1.CO.Cl.[Na+]~[OH-]>>CCc1nc2c(C)cc(C)nc2n1Cc1cc(C)c(OC(C(=O)O)c2cccc(Cl)c2)c(C)c1 | CCc1nc2c(C)cc(C)nc2n1Cc1cc(C)c(OC(C(=O)OC)c2cccc(Cl)c2)c(C)c1.CO.Cl.[Na+].[OH-]>>CCc1nc2c(C)cc(C)nc2n1Cc1cc(C)c(OC(C(=O)O)c2cccc(Cl)c2)c(C)c1 | US05374638_grants | e4020b3c68c796d876da7492c7aa1ce5e340009659777210fad3a8b8 | CO.C[O:24][C:22]([CH:21]([O:20][c:19]1[c:17]([CH3:18])[cH:16][c:15]([CH2:14][n:13]2[c:3]([CH2:2][CH3:1])[n:4][c:5]3[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[n:11][c:12]32)[cH:34][c:32]1[CH3:33])[c:25]1[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]1)=[O:23].Cl.[Na+].[OH-] | [CH3:1][CH2:2][c:3]1[n:4][c:5]2[c:6]([CH3:7])[cH:8][c:9]([CH3:10])[n:11][c:12]2[n:13]1[CH2:14][c:15]1[cH:16][c:17]([CH3:18])[c:19]([O:20][CH:21]([C:22](=[O:23])[OH:24])[c:25]2[cH:26][cH:27][cH:28][c:29]([Cl:30])[cH:31]2)[c:32]([CH3:33])[cH:34]1 | ([C:3]-[C:2](=[O;D1;H0:4])-[OH;D1;+0:1])>>(C-[O;H0;D2;+0:1]-[C:2](-[C:3])=[O;D1;H0:4]) | 0a02d2d47df007d05d29f7b852c5bfe9dcbd7a32224d027cc636bd27 | 1 | 1 | CO.Cl.[Na+].[OH-] | 88 |
181,680 | 630,365 | 1,043,302 | P(Cl)(Cl)(Cl)=O.[Cl:6][C:7]1[C:8]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)=[N:9][CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].CN(C)[CH:22]=[O:23]>>[Cl:6][C:7]1[C:8]([N:13]2[CH:17]=[CH:16][CH:15]=[C:14]2[CH:22]=[O:23])=[N:9][CH:10]=[CH:11][CH:12]=1 | |f:2.3| | US07867949B2_2257 | 2,011 | CN(C)[CH:2]=[O:1].O=P(Cl)(Cl)Cl.[Na+].[OH-].[cH:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[Cl:14]>>[O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[Cl:14] | 0.9468 | CN(C)C=O.Clc1cccnc1-n1cccc1.O=P(Cl)(Cl)Cl.[Na+]~[OH-]>>O=Cc1cccn1-c1ncccc1Cl | CN(C)C=O.Clc1cccnc1-n1cccc1.O=P(Cl)(Cl)Cl.[Na+].[OH-]>>O=Cc1cccn1-c1ncccc1Cl | US07867949B2_2257grants | 4a6db74fe289808fdca4d8f976a4879f28bf19a9c339a5d73ca346db | CN(C)[CH:2]=[O:1].O=P(Cl)(Cl)Cl.[Na+].[OH-].[cH:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[Cl:14] | [O:1]=[CH:2][c:3]1[cH:4][cH:5][cH:6][n:7]1-[c:8]1[n:9][cH:10][cH:11][cH:12][c:13]1[Cl:14] | ([#7;a:3]:[c;H0;D3;+0:4](:[c:5])-[CH;D2;+0:1]=[O;D1;H0:2])>>(C-N(-C)-[CH;D2;+0:1]=[O;D1;H0:2]).([#7;a:3]:[cH;D2;+0:4]:[c:5]) | ed510723a58027934cc530922a15bb4680b6ec41a20fab408e17c010 | 1 | 1 | O=P(Cl)(Cl)Cl.[Na+].[OH-] | 641 |
105,518 | 402,152 | 686,679 | C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>Br>[NH:12]1[CH2:13][CH2:14][CH:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10][CH2:11]1 | null | US06903120B2_0140 | 2,005 | Br.C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[cH:13]1>>[OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[cH:13]1 | 0.955985 | Br.COc1cccc(C2CCNCC2)c1>>Oc1cccc(C2CCNCC2)c1 | Br.COc1cccc(C2CCNCC2)c1>>Oc1cccc(C2CCNCC2)c1 | US06903120B2_0140grants | b4552e48a6882534dfde9d2b8e319dfffacbaaa5da4da89be60ba586 | Br.C[O:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[cH:13]1 | [OH:1][c:2]1[cH:3][cH:4][cH:5][c:6]([CH:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12]2)[cH:13]1 | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | Br | 48 |
370,037 | 760,475 | null | [NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([OH:7])=[O:6].S(=O)(=O)(O)O.[CH2:19](O)[CH3:20]>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[C:5]([O:7][CH2:19][CH3:20])=[O:6] | null | US20090227591A1_0164 | 2,009 | O=S(=O)(O)O.O[C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.[CH3:1][CH2:2][OH:3]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | 0.841691 | CCO.Nc1cc(C(=O)O)cc([N+](=O)[O-])c1.O=S(=O)(O)O>>CCOC(=O)c1cc(N)cc([N+](=O)[O-])c1 | CCO.Nc1cc(C(=O)O)cc([N+](=O)[O-])c1.O=S(=O)(O)O>>CCOC(=O)c1cc(N)cc([N+](=O)[O-])c1 | US20090227591A1_0164apps | b72f3226c65a25f65e55f763b2cceaa8cdf071b05025fc53a404d505 | O=S(=O)(O)O.O[C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1.[CH3:1][CH2:2][OH:3] | [CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([NH2:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | ([C:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[OH;D1;+0:5]) | 462ff262701550e8361ae350b730fe337624136bbbc825e08432a1b4 | 1 | 1 | O=S(=O)(O)O | 33 |
322,682 | 1,048,998 | 1,780,202 | [NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]3[C:17]4[C:22]([CH:23]=[CH:24][C:9]2=3)=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:27]=1[C:28](Cl)=[O:29].IC1C=CC=CC=1C(NCCN1C(=O)CC(=O)NC2C3C(C=CC1=2)=CC=CC=3)=O>>[F:25][C:26]1[C:27]([C:28]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[C:14](=[O:15])[CH2:13][C:12](=[O:16])[NH:11][C:10]4[C:17]5[C:22]([CH:23]=[CH:24][C:9]3=4)=[CH:21][CH:20]=[CH:19][CH:18]=5)=[CH:4][CH:3]=2)=[O:29])=[C:31]([O:35][CH3:36])[CH:32]=[CH:33][CH:34]=1 | null | US09382236B2_0397 | 2,016 | Cl[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[F:8])=[O:11].O=C1CC(=O)N(CCNC(=O)c2ccccc2I)c2ccc3ccccc3c2N1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[C:18](=[O:19])[CH2:20][C:21](=[O:22])[NH:23][c:24]3[c:25]2[cH:26][cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]32)[cH:34][cH:35]1>>[CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[C:18](=[O:19])[CH2:20][C:21](=[O:22])[NH:23][c:24]3[c:25]2[cH:26][cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]32)[cH:34][cH:35]1 | 0.690779 | COc1cccc(F)c1C(=O)Cl.Nc1ccc(N2C(=O)CC(=O)Nc3c2ccc2ccccc32)cc1.O=C1CC(=O)N(CCNC(=O)c2ccccc2I)c2ccc3ccccc3c2N1>>COc1cccc(F)c1C(=O)Nc1ccc(N2C(=O)CC(=O)Nc3c2ccc2ccccc32)cc1 | COc1cccc(F)c1C(=O)Cl.Nc1ccc(N2C(=O)CC(=O)Nc3c2ccc2ccccc32)cc1.O=C1CC(=O)N(CCNC(=O)c2ccccc2I)c2ccc3ccccc3c2N1>>COc1cccc(F)c1C(=O)Nc1ccc(N2C(=O)CC(=O)Nc3c2ccc2ccccc32)cc1 | US09382236B2_0397grants | de3fe2929ae70765521b1a3ab042b3c8a542e4265adfcf44aa335809 | Cl[C:10]([c:9]1[c:3]([O:2][CH3:1])[cH:4][cH:5][cH:6][c:7]1[F:8])=[O:11].O=C1CC(=O)N(CCNC(=O)c2ccccc2I)c2ccc3ccccc3c2N1.[NH2:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[C:18](=[O:19])[CH2:20][C:21](=[O:22])[NH:23][c:24]3[c:25]2[cH:26][cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]32)[cH:34][cH:35]1 | [CH3:1][O:2][c:3]1[cH:4][cH:5][cH:6][c:7]([F:8])[c:9]1[C:10](=[O:11])[NH:12][c:13]1[cH:14][cH:15][c:16]([N:17]2[C:18](=[O:19])[CH2:20][C:21](=[O:22])[NH:23][c:24]3[c:25]2[cH:26][cH:27][c:28]2[cH:29][cH:30][cH:31][cH:32][c:33]32)[cH:34][cH:35]1 | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[c:5])>>(Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[c:5]) | 81bbe9d480d200be1437e9ca625a57474abf80dfdc397cf8e383daca | 1 | 1 | O=C1CC(=O)N(CCNC(=O)c2ccccc2I)c2ccc3ccccc3c2N1 | 11 |
382,040 | 964,803 | null | [NH2:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C@H:3]1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].[Cl:23][CH2:24][CH2:25][CH2:26][C:27](Cl)=[O:28]>C(Cl)Cl>[Cl:23][CH2:24][CH2:25][CH2:26][C:27]([NH:1][C@@H:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][C@H:3]1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[O:28] | null | US20100272680A1_0686 | 2,010 | ClCCl.Cl[C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH2:12])[C@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1>>[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH:12][C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18])[C@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1 | 0.150149 | CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](O[Si](C)(C)C(C)(C)C)C1.ClCCl.O=C(Cl)CCCCl>>CC(C)(C)OC(=O)N1CC[C@@H](NC(=O)CCCCl)[C@H](O[Si](C)(C)C(C)(C)C)C1 | CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](O[Si](C)(C)C(C)(C)C)C1.ClCCl.O=C(Cl)CCCCl>>CC(C)(C)OC(=O)N1CC[C@@H](NC(=O)CCCCl)[C@H](O[Si](C)(C)C(C)(C)C)C1 | US20100272680A1_0686apps | 8f0c06238183d62cbfb18c7885289139637f0201d9a82a746c6bba32 | ClCCl.Cl[C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18].[CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH2:12])[C@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1 | [CH3:1][C:2]([CH3:3])([CH3:4])[O:5][C:6](=[O:7])[N:8]1[CH2:9][CH2:10][C@@H:11]([NH:12][C:13](=[O:14])[CH2:15][CH2:16][CH2:17][Cl:18])[C@H:19]([O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27])[CH2:28]1 | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH2;D1;+0:5]) | 493dfbb0afd083041fcf14557ee7dc8217381b2f2e0ce03b2961712e | 1 | 1 | ClCCl | 45 |
314,716 | 1,023,342 | 1,731,921 | [NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([NH:8][C:9]2[C:10]3[CH:17]=[CH:16][N:15]([S:18]([C:21]4[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:11]=3[N:12]=[CH:13][N:14]=2)[CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Cl:49][C:50]1[CH:51]=[C:52]([NH:57][CH2:58][C:59](O)=[O:60])[CH:53]=[C:54]([Cl:56])[CH:55]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Cl:49][C:50]1[CH:51]=[C:52]([NH:57][CH2:58][C:59]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]([NH:8][C:9]3[C:10]4[CH:17]=[CH:16][N:15]([S:18]([C:21]5[CH:22]=[CH:23][C:24]([CH3:25])=[CH:26][CH:27]=5)(=[O:19])=[O:20])[C:11]=4[N:12]=[CH:13][N:14]=3)[CH2:2]2)=[O:60])[CH:53]=[C:54]([Cl:56])[CH:55]=1 | null | US09273028B2_0498 | 2,016 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.O[C:21](=[O:22])[CH2:23][NH:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]1.On1nnc2ccccc21.[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][c:12]3[c:13]([NH:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:33]4)[n:34][cH:35][n:36][c:37]23)[cH:38][cH:39]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][c:12]3[c:13]([NH:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][N:20]([C:21](=[O:22])[CH2:23][NH:24][c:25]5[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]5)[CH2:33]4)[n:34][cH:35][n:36][c:37]23)[cH:38][cH:39]1 | 0.497295 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cc1ccc(S(=O)(=O)n2ccc3c(NC4CCCCNC4)ncnc32)cc1.O=C(O)CNc1cc(Cl)cc(Cl)c1.On1nnc2ccccc21>>Cc1ccc(S(=O)(=O)n2ccc3c(NC4CCCCN(C(=O)CNc5cc(Cl)cc(Cl)c5)C4)ncnc32)cc1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.Cc1ccc(S(=O)(=O)n2ccc3c(NC4CCCCNC4)ncnc32)cc1.O=C(O)CNc1cc(Cl)cc(Cl)c1.On1nnc2ccccc21>>Cc1ccc(S(=O)(=O)n2ccc3c(NC4CCCCN(C(=O)CNc5cc(Cl)cc(Cl)c5)C4)ncnc32)cc1 | US09273028B2_0498grants | 504a97f4d02dcd193baacf5b64f4856f0b374c075436586e75eec771 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.O[C:21](=[O:22])[CH2:23][NH:24][c:25]1[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]1.On1nnc2ccccc21.[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][c:12]3[c:13]([NH:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:33]4)[n:34][cH:35][n:36][c:37]23)[cH:38][cH:39]1 | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[n:9]2[cH:10][cH:11][c:12]3[c:13]([NH:14][CH:15]4[CH2:16][CH2:17][CH2:18][CH2:19][N:20]([C:21](=[O:22])[CH2:23][NH:24][c:25]5[cH:26][c:27]([Cl:28])[cH:29][c:30]([Cl:31])[cH:32]5)[CH2:33]4)[n:34][cH:35][n:36][c:37]23)[cH:38][cH:39]1 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(O-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 0f35e4698af78868189072042f755bea621b23e196ec3dd2372ca253 | 1 | 1 | CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.CCOC(C)=O.CN(C)C=O.On1nnc2ccccc21 | 146 |
139,875 | 505,676 | 848,898 | C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]=2[CH:29]=[O:30])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(#N)C.CCOCC>ClCCl>[N:11]1([C:14]2[N:22]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:16]3[C:15]=2[CH:29]=[O:30])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1 | null | US07405300B2_0474 | 2,008 | CC#N.CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([c:4]2[c:3]([CH:2]=[O:1])[c:23]3[c:18]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[n:19][cH:20][cH:21][cH:22]3)[CH2:10][CH2:9]1.CCOCC.ClCCl.O=C(O)C(F)(F)F>>[O:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[n:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]2[n:19][cH:20][cH:21][cH:22][c:23]12 | 0.905188 | CC#N.CC(C)(C)OC(=O)N1CCN(c2c(C=O)c3cccnc3n2-c2cccnc2)CC1.CCOCC.ClCCl.O=C(O)C(F)(F)F>>O=Cc1c(N2CCNCC2)n(-c2cccnc2)c2ncccc12 | CC#N.CC(C)(C)OC(=O)N1CCN(c2c(C=O)c3cccnc3n2-c2cccnc2)CC1.CCOCC.ClCCl.O=C(O)C(F)(F)F>>O=Cc1c(N2CCNCC2)n(-c2cccnc2)c2ncccc12 | US07405300B2_0474grants | 380f41b55e948ed02da3bba97edb79d0f209d862eea9419dbbe081cb | CC#N.CC(C)(C)OC(=O)[N:8]1[CH2:7][CH2:6][N:5]([c:4]2[c:3]([CH:2]=[O:1])[c:23]3[c:18]([n:11]2-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[n:19][cH:20][cH:21][cH:22]3)[CH2:10][CH2:9]1.CCOCC.ClCCl.O=C(O)C(F)(F)F | [O:1]=[CH:2][c:3]1[c:4]([N:5]2[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]2)[n:11](-[c:12]2[cH:13][cH:14][cH:15][n:16][cH:17]2)[c:18]2[n:19][cH:20][cH:21][cH:22][c:23]12 | ([C:2]-[NH;D2;+0:1]-[C:3])>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]) | 55396c1492cc3823f0701ef923544f9f4c1af584b69f4ce5650dc5ae | 1 | 1 | CC#N.CCOCC.ClCCl.O=C(O)C(F)(F)F | 575 |
74,215 | 303,731 | 514,335 | [F:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(OCC)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[CH2:4][Br:31] | null | US06245761B1_ | 2,001 | BrC(Br)(Br)[Br:10].CCOCC.O[CH2:9][c:8]1[c:2]([F:1])[cH:3][cH:4][c:5]([Cl:6])[cH:7]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>[F:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[CH2:9][Br:10] | 0.252368 | BrC(Br)(Br)Br.CCOCC.OCc1cc(Cl)ccc1F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1ccc(Cl)cc1CBr | BrC(Br)(Br)Br.CCOCC.OCc1cc(Cl)ccc1F.c1ccc(P(c2ccccc2)c2ccccc2)cc1>>Fc1ccc(Cl)cc1CBr | US06245761B1_grants | 967a61ffbc2d960eac016b96907b3216a340675f10c133ab38986cfd | BrC(Br)(Br)[Br:10].CCOCC.O[CH2:9][c:8]1[c:2]([F:1])[cH:3][cH:4][c:5]([Cl:6])[cH:7]1.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | [F:1][c:2]1[cH:3][cH:4][c:5]([Cl:6])[cH:7][c:8]1[CH2:9][Br:10] | ([Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[c:3])>>(Br-C(-Br)(-Br)-[Br;H0;D1;+0:1]).(O-[CH2;D2;+0:2]-[c:3]) | 8505341f55ce79398eac32d5026ef69fb4643eb768c31986300ce346 | 1 | 1 | CCOCC.c1ccc(P(c2ccccc2)c2ccccc2)cc1 | 750 |
182,814 | 633,891 | 1,048,706 | [C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]N1C(=O)CCC1=O>C(O)(=O)C.CO>[Br:20][C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3 | null | US07880019B2_0292 | 2,011 | CC(=O)O.CO.O=C1CCC(=O)N1[Br:1].[cH:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[n:14]2-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1>>[Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[n:14]2-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | 0.516441 | CC(=O)O.CO.O=C1CCC(=O)N1Br.c1ccc(-n2c3ccccc3c3ccccc32)cc1>>Brc1ccc2c(c1)c1ccccc1n2-c1ccccc1 | CC(=O)O.CO.O=C1CCC(=O)N1Br.c1ccc(-n2c3ccccc3c3ccccc32)cc1>>Brc1ccc2c(c1)c1ccccc1n2-c1ccccc1 | US07880019B2_0292grants | 5f36d4465c37b1660bb4635cbf03b56c16679171f09c0ee84caaae61 | CC(=O)O.CO.O=C1CCC(=O)N1[Br:1].[cH:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[n:14]2-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | [Br:1][c:2]1[cH:3][cH:4][c:5]2[c:6]([cH:7]1)[c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[n:14]2-[c:15]1[cH:16][cH:17][cH:18][cH:19][cH:20]1 | ([Br;H0;D1;+0:1]-[c;H0;D3;+0:3](:[c:2]):[c:4])>>(O=C1-C-C-C(=O)-N-1-[Br;H0;D1;+0:1]).([c:2]:[cH;D2;+0:3]:[c:4]) | 04aac57316494f5621172b80523cd496e017f4d0104703ad33b2fa4b | 1 | 1 | CC(=O)O.CO | 4 |
251,594 | 834,096 | 1,383,736 | [Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(Cl)(=O)C(Cl)=O.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][NH2:43])=[CH:37][CH:36]=1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:22])[C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17](=[O:19])[NH:43][CH2:42][CH2:41][C:38]3[CH:39]=[CH:40][C:35]([Cl:34])=[CH:36][CH:37]=3)=[CH:20][CH:21]=1)[O:8][CH2:7][CH2:6][CH:5]2[C:23]([O:25][CH2:26][CH3:27])=[O:24] | null | US08569522B2_0797 | 2,013 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:21]([c:20]1[cH:19][cH:18][c:17]([O:16][c:15]2[c:13]([Cl:14])[cH:12][c:11]3[c:10]([c:35]2[Cl:36])[O:9][CH2:8][CH2:7][CH:6]3[C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:34][cH:33]1)=[O:22].[NH2:23][CH2:24][CH2:25][c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][c:17]1[cH:18][cH:19][c:20]([C:21](=[O:22])[NH:23][CH2:24][CH2:25][c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[cH:33][cH:34]1)[c:35]2[Cl:36] | 0.915167 | CCN(C(C)C)C(C)C.CCOC(=O)C1CCOc2c1cc(Cl)c(Oc1ccc(C(=O)O)cc1)c2Cl.CN(C)C=O.ClCCl.NCCc1ccc(Cl)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C1CCOc2c1cc(Cl)c(Oc1ccc(C(=O)NCCc3ccc(Cl)cc3)cc1)c2Cl | CCN(C(C)C)C(C)C.CCOC(=O)C1CCOc2c1cc(Cl)c(Oc1ccc(C(=O)O)cc1)c2Cl.CN(C)C=O.ClCCl.NCCc1ccc(Cl)cc1.O=C(Cl)C(=O)Cl>>CCOC(=O)C1CCOc2c1cc(Cl)c(Oc1ccc(C(=O)NCCc3ccc(Cl)cc3)cc1)c2Cl | US08569522B2_0797grants | 30607f26c607bf4ef08b9f689e9cd67cad2011494fcc54f0a5834c6b | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl.O[C:21]([c:20]1[cH:19][cH:18][c:17]([O:16][c:15]2[c:13]([Cl:14])[cH:12][c:11]3[c:10]([c:35]2[Cl:36])[O:9][CH2:8][CH2:7][CH:6]3[C:4]([O:3][CH2:2][CH3:1])=[O:5])[cH:34][cH:33]1)=[O:22].[NH2:23][CH2:24][CH2:25][c:26]1[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]1 | [CH3:1][CH2:2][O:3][C:4](=[O:5])[CH:6]1[CH2:7][CH2:8][O:9][c:10]2[c:11]1[cH:12][c:13]([Cl:14])[c:15]([O:16][c:17]1[cH:18][cH:19][c:20]([C:21](=[O:22])[NH:23][CH2:24][CH2:25][c:26]3[cH:27][cH:28][c:29]([Cl:30])[cH:31][cH:32]3)[cH:33][cH:34]1)[c:35]2[Cl:36] | ([C:4]-[NH;D2;+0:5]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3])>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([C:4]-[NH2;D1;+0:5]) | 4b62c30a3b92b9941a5ddfdb3fbb597241af09409f8fb78aee5317d4 | 1 | 1 | CCN(C(C)C)C(C)C.CN(C)C=O.ClCCl.O=C(Cl)C(=O)Cl | 334 |
346,550 | 417,797 | null | [S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:11]=[C:10](Cl)[C:9]([CH2:13][CH3:14])=[C:8]([CH3:15])[N:7]=1.[NH2:16][CH2:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.N12CCCN=C1CCCCC2.Cl>C(O)CCC.C(N(CC)CC)C>[CH2:13]([C:9]1[C:10]([NH:16][CH2:17][CH2:18][C:19]2[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=2)=[N:11][C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7][C:8]=1[CH3:15])[CH3:14] | null | US20060293343A1_0513 | 2,006 | C1CCC2=NCCCN2CC1.CCCCO.CCN(CC)CC.Cl.Cl[c:14]1[c:3]([CH2:2][CH3:1])[c:4]([CH3:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[n:13]1.[NH2:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1>>[CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[n:13][c:14]1[NH:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1 | 0.909144 | C1CCC2=NCCCN2CC1.CCCCO.CCN(CC)CC.CCc1c(C)nc(-c2cccs2)nc1Cl.Cl.NCCc1ccc(C(=O)O)cc1>>CCc1c(C)nc(-c2cccs2)nc1NCCc1ccc(C(=O)O)cc1 | C1CCC2=NCCCN2CC1.CCCCO.CCN(CC)CC.CCc1c(C)nc(-c2cccs2)nc1Cl.Cl.NCCc1ccc(C(=O)O)cc1>>CCc1c(C)nc(-c2cccs2)nc1NCCc1ccc(C(=O)O)cc1 | US20060293343A1_0513apps | af2f5fb823b42d489c3b202b155398cd0fa023acee15f542a89e48ad | C1CCC2=NCCCN2CC1.CCCCO.CCN(CC)CC.Cl.Cl[c:14]1[c:3]([CH2:2][CH3:1])[c:4]([CH3:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[n:13]1.[NH2:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1 | [CH3:1][CH2:2][c:3]1[c:4]([CH3:5])[n:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][s:12]2)[n:13][c:14]1[NH:15][CH2:16][CH2:17][c:18]1[cH:19][cH:20][c:21]([C:22](=[O:23])[OH:24])[cH:25][cH:26]1 | ([C:7]-[NH;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C:7]-[NH2;D1;+0:8]) | 9ba15a7b9393a64a7fde93acd4e7b07a21f5e92fd01af7815d1917a2 | 1 | 1 | C1CCC2=NCCCN2CC1.CCCCO.CCN(CC)CC.Cl | 166 |
161,881 | 571,581 | 952,702 | [F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8] | |f:2.3.4| | US07652009B2_0644 | 2,010 | CN1CCCC1=O.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][cH:18]2)[cH:19][c:20]1[F:21].O.O=C([O-])[O-].Sc1ccccc1.[K+].[K+]>>[OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][cH:18]2)[cH:19][c:20]1[F:21] | 0.836421 | CN1CCCC1=O.COc1ccc(-c2cnc(Nc3ccccc3)nc2)cc1F.O.O=C([O-])[O-]~[K+]~[K+].Sc1ccccc1>>Oc1ccc(-c2cnc(Nc3ccccc3)nc2)cc1F | CN1CCCC1=O.COc1ccc(-c2cnc(Nc3ccccc3)nc2)cc1F.O.O=C([O-])[O-].Sc1ccccc1.[K+].[K+]>>Oc1ccc(-c2cnc(Nc3ccccc3)nc2)cc1F | US07652009B2_0644grants | 0e3ead25d4cd9618cf46efb2b458d5a5017c1842dd2854fffd07690b | CN1CCCC1=O.C[O:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][cH:18]2)[cH:19][c:20]1[F:21].O.O=C([O-])[O-].Sc1ccccc1.[K+].[K+] | [OH:1][c:2]1[cH:3][cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]([NH:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[n:17][cH:18]2)[cH:19][c:20]1[F:21] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | CN1CCCC1=O.O.O=C([O-])[O-].Sc1ccccc1.[K+].[K+] | 48 |
67,125 | 280,080 | 475,091 | [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[C:10]=2[C:28]([O:30]CC)=[O:29])=[CH:5][CH:4]=1.[OH-].[Na+].O>CCO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]4[O:25][CH2:26][O:27][C:21]=4[CH:20]=3)[C:10]=2[C:28]([OH:30])=[O:29])=[CH:7][CH:8]=1 | |f:1.2| | US06075037_ | 2,000 | CCO.CC[O:11][C:9]([c:8]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[c:28]2[c:23]([n:12]1[CH2:13][c:14]1[cH:15][cH:16][c:17]3[c:18]([cH:19]1)[O:20][CH2:21][O:22]3)[n:24][cH:25][cH:26][cH:27]2)=[O:10].O.[Na+].[OH-]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([C:9](=[O:10])[OH:11])[n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][CH2:21][O:22]4)[c:23]3[n:24][cH:25][cH:26][cH:27][c:28]23)[cH:29][cH:30]1 | 0.884768 | CCO.CCOC(=O)c1c(-c2ccc(OC)cc2)c2cccnc2n1Cc1ccc2c(c1)OCO2.O.[Na+]~[OH-]>>COc1ccc(-c2c(C(=O)O)n(Cc3ccc4c(c3)OCO4)c3ncccc23)cc1 | CCO.CCOC(=O)c1c(-c2ccc(OC)cc2)c2cccnc2n1Cc1ccc2c(c1)OCO2.O.[Na+].[OH-]>>COc1ccc(-c2c(C(=O)O)n(Cc3ccc4c(c3)OCO4)c3ncccc23)cc1 | US06075037_grants | 26a45a89196ff7109decd336515298cb3ba9b5727491659a6511fa7e | CCO.CC[O:11][C:9]([c:8]1[c:7](-[c:6]2[cH:5][cH:4][c:3]([O:2][CH3:1])[cH:30][cH:29]2)[c:28]2[c:23]([n:12]1[CH2:13][c:14]1[cH:15][cH:16][c:17]3[c:18]([cH:19]1)[O:20][CH2:21][O:22]3)[n:24][cH:25][cH:26][cH:27]2)=[O:10].O.[Na+].[OH-] | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6](-[c:7]2[c:8]([C:9](=[O:10])[OH:11])[n:12]([CH2:13][c:14]3[cH:15][cH:16][c:17]4[c:18]([cH:19]3)[O:20][CH2:21][O:22]4)[c:23]3[n:24][cH:25][cH:26][cH:27][c:28]23)[cH:29][cH:30]1 | ([O;D1;H0:3]=[C:2](-[OH;D1;+0:1])-[c:4])>>(C-C-[O;H0;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4]) | b8d35231a9d964a0bcde41cb860d8e6c4726c2823ff5946d3ed0c3c9 | 1 | 1 | CCO.O.[Na+].[OH-] | 171 |
25,682 | 120,866 | 195,757 | Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH:12]=[CH:11][N:10]=[CH:9]2)[CH:3]=1.[Na].[CH3:14][OH:15]>>[N:8]1([C:4]2[CH:3]=[C:2]([O:15][CH3:14])[N:7]=[CH:6][N:5]=2)[CH:12]=[CH:11][N:10]=[CH:9]1 | |^1:12| | US04849424_ | 1,989 | Cl[c:3]1[cH:4][c:5](-[n:6]2[cH:7][cH:8][n:9][cH:10]2)[n:11][cH:12][n:13]1.[CH3:1][OH:2].[Na]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[n:6]2[cH:7][cH:8][n:9][cH:10]2)[n:11][cH:12][n:13]1 | 0.987189 | CO.Clc1cc(-n2ccnc2)ncn1.[Na]>>COc1cc(-n2ccnc2)ncn1 | CO.Clc1cc(-n2ccnc2)ncn1.[Na]>>COc1cc(-n2ccnc2)ncn1 | US04849424_grants | 7f9a4fb0d90cc499aedd04ef232a576dc4ce7bd14df01516d0582793 | Cl[c:3]1[cH:4][c:5](-[n:6]2[cH:7][cH:8][n:9][cH:10]2)[n:11][cH:12][n:13]1.[CH3:1][OH:2].[Na] | [CH3:1][O:2][c:3]1[cH:4][c:5](-[n:6]2[cH:7][cH:8][n:9][cH:10]2)[n:11][cH:12][n:13]1 | ([C;D1;H3:7]-[O;H0;D2;+0:8]-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1)>>(Cl-[c;H0;D3;+0:1]1:[#7;a:2]:[c:3]:[#7;a:4]:[c:5]:[c:6]:1).([C;D1;H3:7]-[OH;D1;+0:8]) | 5143b901619ce0acc66a8a625982dda04978c2b35cb026eacddddf7e | 1 | 1 | [Na] | 653 |
382,944 | 979,292 | null | [CH3:1][O:2][C:3]1[C:4]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][C:16]([C:22](O)=[O:23])=[CH:17][CH:18]=3)[NH:13][C:12]2=[S:25])=[N:5][CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH2:31].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(#N)C.C(OCC)(=O)C>[Cl:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=1)[CH2:30][NH:31][C:22]([C:16]1[CH:15]=[C:14]2[C:19]([C:20](=[O:21])[N:11]([C:4]3[C:3]([O:2][CH3:1])=[CH:8][C:7]([O:9][CH3:10])=[CH:6][N:5]=3)[C:12](=[S:25])[NH:13]2)=[CH:18][CH:17]=1)=[O:23] | |f:3.4| | US20100298324A1_0099 | 2,010 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O[C:14]([c:13]1[cH:12][c:11]2[nH:10][c:8](=[S:9])[n:7](-[c:6]3[n:5][cH:4][c:3]([O:2][CH3:1])[cH:33][c:30]3[O:31][CH3:32])[c:28](=[O:29])[c:27]2[cH:26][cH:25]1)=[O:15].[NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]1>>[CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[n:7]2[c:8](=[S:9])[nH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[NH:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]4)[cH:25][cH:26][c:27]3[c:28]2=[O:29])[c:30]([O:31][CH3:32])[cH:33]1 | 0.960213 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C~F[B-](F)(F)F.COc1cnc(-n2c(=S)[nH]c3cc(C(=O)O)ccc3c2=O)c(OC)c1.NCc1cccc(Cl)c1>>COc1cnc(-n2c(=S)[nH]c3cc(C(=O)NCc4cccc(Cl)c4)ccc3c2=O)c(OC)c1 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.COc1cnc(-n2c(=S)[nH]c3cc(C(=O)O)ccc3c2=O)c(OC)c1.F[B-](F)(F)F.NCc1cccc(Cl)c1>>COc1cnc(-n2c(=S)[nH]c3cc(C(=O)NCc4cccc(Cl)c4)ccc3c2=O)c(OC)c1 | US20100298324A1_0099apps | 9ff5ac57d61f0e7f64e25edae4f77721a6b802f56a31a1d2913d3b0b | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F.O[C:14]([c:13]1[cH:12][c:11]2[nH:10][c:8](=[S:9])[n:7](-[c:6]3[n:5][cH:4][c:3]([O:2][CH3:1])[cH:33][c:30]3[O:31][CH3:32])[c:28](=[O:29])[c:27]2[cH:26][cH:25]1)=[O:15].[NH2:16][CH2:17][c:18]1[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]1 | [CH3:1][O:2][c:3]1[cH:4][n:5][c:6](-[n:7]2[c:8](=[S:9])[nH:10][c:11]3[cH:12][c:13]([C:14](=[O:15])[NH:16][CH2:17][c:18]4[cH:19][cH:20][cH:21][c:22]([Cl:23])[cH:24]4)[cH:25][cH:26][c:27]3[c:28]2=[O:29])[c:30]([O:31][CH3:32])[cH:33]1 | ([O;D1;H0:2]=[C;H0;D3;+0:1](-[c:3])-[NH;D2;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1)>>(O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3]).([NH2;D1;+0:4]-[C:5]-[c:6]1:[c:7]:[c:8]:[c:9]:[c:10]:[c:11]:1) | 1e906db6a77b0514fde5b7203388f1047e0cbf77350c2b0657491a6b | 1 | 1 | CC#N.CCN(C(C)C)C(C)C.CCOC(C)=O.CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F | 753 |
91,428 | 359,453 | 612,314 | Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:12][CH:11]=2)[N:3]=1.C(OC1C=CC(CO)=CC=1)C1C=CC=CC=1.[NH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1.C([O-])([O-])=O.[K+].[K+]>>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:4]2[CH:5]=[N:6][CH:7]=[C:2]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)[N:3]=2)=[CH:11][CH:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1 | |f:3.4.5| | US06593330B2_ | 2,003 | Cl[c:17]1[cH:16][n:15][cH:14][c:13]([O:12][CH2:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:28][cH:27]3)[cH:26][cH:25]2)[n:24]1.O=C([O-])[O-].OCc1ccc(OCc2ccccc2)cc1.[K+].[K+].[NH:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1>>[cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][O:12][c:13]3[cH:14][n:15][cH:16][c:17]([N:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)[n:24]3)[cH:25][cH:26]2)[cH:27][cH:28]1 | 0.235438 | C1CNCCN1.Clc1cncc(OCc2ccc(OCc3ccccc3)cc2)n1.O=C([O-])[O-]~[K+]~[K+].OCc1ccc(OCc2ccccc2)cc1>>c1ccc(COc2ccc(COc3cncc(N4CCNCC4)n3)cc2)cc1 | C1CNCCN1.Clc1cncc(OCc2ccc(OCc3ccccc3)cc2)n1.O=C([O-])[O-].OCc1ccc(OCc2ccccc2)cc1.[K+].[K+]>>c1ccc(COc2ccc(COc3cncc(N4CCNCC4)n3)cc2)cc1 | US06593330B2_grants | 13bf1367fcc5881847bc05e7e33ecc01c92544bc4805a3b9a91a67a7 | Cl[c:17]1[cH:16][n:15][cH:14][c:13]([O:12][CH2:11][c:10]2[cH:9][cH:8][c:7]([O:6][CH2:5][c:4]3[cH:3][cH:2][cH:1][cH:28][cH:27]3)[cH:26][cH:25]2)[n:24]1.O=C([O-])[O-].OCc1ccc(OCc2ccccc2)cc1.[K+].[K+].[NH:18]1[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]1 | [cH:1]1[cH:2][cH:3][c:4]([CH2:5][O:6][c:7]2[cH:8][cH:9][c:10]([CH2:11][O:12][c:13]3[cH:14][n:15][cH:16][c:17]([N:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)[n:24]3)[cH:25][cH:26]2)[cH:27][cH:28]1 | ([#7;a:4]:[c:3]:[c;H0;D3;+0:1](:[#7;a:2])-[N;H0;D3;+0:6](-[C:5])-[C:7])>>(Cl-[c;H0;D3;+0:1](:[#7;a:2]):[c:3]:[#7;a:4]).([C:5]-[NH;D2;+0:6]-[C:7]) | 3dc06bda2af537840489d5b42deeb79863a93db85840f14ac98194e8 | 1 | 1 | O=C([O-])[O-].OCc1ccc(OCc2ccccc2)cc1.[K+].[K+] | 505 |
123,060 | 454,610 | 770,984 | [CH2:1]([O:8][C:9](=[O:48])[N:10]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][C:25](=[O:47])[C:26]2[CH:31]=[CH:30][C:29]([CH2:32][N:33](C(OC(C)(C)C)=O)[CH2:34][C:35]3[NH:36][CH:37]=[CH:38][N:39]=3)=[CH:28][CH:27]=2)=[CH:20][CH:19]=1)[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO>[CH2:1]([O:8][C:9](=[O:48])[N:10]([CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([NH:24][C:25](=[O:47])[C:26]2[CH:31]=[CH:30][C:29]([CH2:32][NH:33][CH2:34][C:35]3[NH:39][CH:38]=[CH:37][N:36]=3)=[CH:28][CH:27]=2)=[CH:22][CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1 | |f:1.2| | US07176227B2_0929 | 2,007 | C1COCCO1.CC(C)(C)OC(=O)[N:33]([CH2:32][c:31]1[cH:30][cH:29][c:28]([C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[cH:41][cH:40]1)[CH2:34][c:35]1[n:36][cH:37][cH:38][nH:39]1.CO.Cl>>[O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1)[c:28]1[cH:29][cH:30][c:31]([CH2:32][NH:33][CH2:34][c:35]2[n:36][cH:37][cH:38][nH:39]2)[cH:40][cH:41]1 | 0.698522 | C1COCCO1~Cl.CC(C)(C)OC(=O)N(Cc1ccc(C(=O)Nc2ccc(CN(C(=O)OCc3ccccc3)C3CCCCC3)cc2)cc1)Cc1ncc[nH]1.CO>>O=C(Nc1ccc(CN(C(=O)OCc2ccccc2)C2CCCCC2)cc1)c1ccc(CNCc2ncc[nH]2)cc1 | C1COCCO1.CC(C)(C)OC(=O)N(Cc1ccc(C(=O)Nc2ccc(CN(C(=O)OCc3ccccc3)C3CCCCC3)cc2)cc1)Cc1ncc[nH]1.CO.Cl>>O=C(Nc1ccc(CN(C(=O)OCc2ccccc2)C2CCCCC2)cc1)c1ccc(CNCc2ncc[nH]2)cc1 | US07176227B2_0929grants | 9fe72cefccb1cc6dc25276887a888f24dadee2fff6dece93054d5876 | C1COCCO1.CC(C)(C)OC(=O)[N:33]([CH2:32][c:31]1[cH:30][cH:29][c:28]([C:2](=[O:1])[NH:3][c:4]2[cH:5][cH:6][c:7]([CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]3[cH:15][cH:16][cH:17][cH:18][cH:19]3)[CH:20]3[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]3)[cH:26][cH:27]2)[cH:41][cH:40]1)[CH2:34][c:35]1[n:36][cH:37][cH:38][nH:39]1.CO.Cl | [O:1]=[C:2]([NH:3][c:4]1[cH:5][cH:6][c:7]([CH2:8][N:9]([C:10](=[O:11])[O:12][CH2:13][c:14]2[cH:15][cH:16][cH:17][cH:18][cH:19]2)[CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[cH:26][cH:27]1)[c:28]1[cH:29][cH:30][c:31]([CH2:32][NH:33][CH2:34][c:35]2[n:36][cH:37][cH:38][nH:39]2)[cH:40][cH:41]1 | ([C:2]-[NH;D2;+0:1]-[C:3]-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1)>>(C-C(-C)(-C)-O-C(=O)-[N;H0;D3;+0:1](-[C:2])-[C:3]-[c:4]1:[c:5]:[c:6]:[c:7]:[c:8]:[c:9]:1) | 06fc5d33cd203f280224fba968abce25e3d9605f712acfb05016df3b | 1 | 1 | C1COCCO1.CO.Cl | 887 |
112,880 | 424,296 | 723,446 | [CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3]1.[CH3:13][NH2:14].[BH4-].[Na+]>CO>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][NH:14][CH3:13])=[CH:3]1 | |f:2.3| | US07049310B2_0260 | 2,006 | CO.O=[CH:3][c:4]1[cH:5][n:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.[BH4-].[CH3:1][NH2:2].[Na+]>>[CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | 0.947477 | CN.CO.Cn1cc(C=O)c2ccccc21.[BH4-]~[Na+]>>CNCc1cn(C)c2ccccc12 | CN.CO.Cn1cc(C=O)c2ccccc21.[BH4-].[Na+]>>CNCc1cn(C)c2ccccc12 | US07049310B2_0260grants | 2dfddb05a905f8bc5ad94d59d4a4052c6e597220df1a6ff8f8096e33 | CO.O=[CH:3][c:4]1[cH:5][n:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12.[BH4-].[CH3:1][NH2:2].[Na+] | [CH3:1][NH:2][CH2:3][c:4]1[cH:5][n:6]([CH3:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][c:13]12 | ([#7;a:4]:[c:3]:[c:2]-[CH2;D2;+0:1]-[NH;D2;+0:6]-[C;D1;H3:5])>>(O=[CH;D2;+0:1]-[c:2]:[c:3]:[#7;a:4]).([C;D1;H3:5]-[NH2;D1;+0:6]) | 621e21e4ce8173d36ef3cda1008da6d0624d2a74d791d6ff5340e475 | 1 | 1 | CO.[BH4-].[Na+] | 441 |
292,432 | 952,061 | 1,598,147 | C(N(CC)CC)C.[CH3:8][C:9]1[N:10]([CH2:20][CH2:21][OH:22])[CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=1.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>ClCCl.O>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:22][CH2:21][CH2:20][N:10]2[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:13]=[C:9]2[CH3:8])(=[O:31])=[O:30])=[CH:25][CH:24]=1 | null | US08993574B2_0789 | 2,015 | CCN(CC)CC.ClCCl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:25][cH:24]1)(=[O:7])=[O:8].O.[OH:9][CH2:10][CH2:11][n:12]1[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][c:22]1[CH3:23]>>[CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[CH3:23])[cH:24][cH:25]1 | 0.519481 | CCN(CC)CC.Cc1cc(-c2ccccc2)cn1CCO.Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.O>>Cc1ccc(S(=O)(=O)OCCn2cc(-c3ccccc3)cc2C)cc1 | CCN(CC)CC.Cc1cc(-c2ccccc2)cn1CCO.Cc1ccc(S(=O)(=O)Cl)cc1.ClCCl.O>>Cc1ccc(S(=O)(=O)OCCn2cc(-c3ccccc3)cc2C)cc1 | US08993574B2_0789grants | 006f4043761df119260b05aee0eac1c0db52e03baa0bf30c32dd8300 | CCN(CC)CC.ClCCl.Cl[S:6]([c:5]1[cH:4][cH:3][c:2]([CH3:1])[cH:25][cH:24]1)(=[O:7])=[O:8].O.[OH:9][CH2:10][CH2:11][n:12]1[cH:13][c:14](-[c:15]2[cH:16][cH:17][cH:18][cH:19][cH:20]2)[cH:21][c:22]1[CH3:23] | [CH3:1][c:2]1[cH:3][cH:4][c:5]([S:6](=[O:7])(=[O:8])[O:9][CH2:10][CH2:11][n:12]2[cH:13][c:14](-[c:15]3[cH:16][cH:17][cH:18][cH:19][cH:20]3)[cH:21][c:22]2[CH3:23])[cH:24][cH:25]1 | ([C:5]-[O;H0;D2;+0:6]-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4])>>(Cl-[S;H0;D4;+0:1](=[O;D1;H0:2])(=[O;D1;H0:3])-[c:4]).([C:5]-[OH;D1;+0:6]) | 2a680215c1c69f116045ff1696194ac3ca890d5406b0abc3856bedc8 | 1 | 1 | CCN(CC)CC.ClCCl.O | 197 |
261,731 | 863,567 | 1,437,364 | CCN(CC)CC.Br[C:9]1[CH:10]=[C:11]([NH:15][C:16](=[O:24])[CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH:12]=[CH:13][CH:14]=1.[CH2:25]([NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:26]=[CH2:27].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:18]([CH:17]([CH2:21][CH2:22][CH3:23])[C:16]([NH:15][C:11]1[CH:10]=[C:9](/[CH:27]=[CH:26]/[CH2:25][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH:14]=[CH:13][CH:12]=1)=[O:24])[CH2:19][CH3:20] | |f:5.6.7| | US08674137B2_1551 | 2,014 | Br[c:15]1[cH:14][cH:13][cH:12][c:11]([NH:10][C:8]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:27]1.CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CN(C)C=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.[CH2:16]=[CH:17][CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].[Pd+2]>>[CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][cH:14][c:15](/[CH:16]=[CH:17]/[CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27]1 | 0.350256 | C=CCNC(=O)OC(C)(C)C.CC(=O)[O-]~CC(=O)[O-]~[Pd+2].CCCC(CCC)C(=O)Nc1cccc(Br)c1.CCN(CC)CC.CN(C)C=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C>>CCCC(CCC)C(=O)Nc1cccc(/C=C/CNC(=O)OC(C)(C)C)c1 | C=CCNC(=O)OC(C)(C)C.CC(=O)[O-].CC(=O)[O-].CCCC(CCC)C(=O)Nc1cccc(Br)c1.CCN(CC)CC.CN(C)C=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.[Pd+2]>>CCCC(CCC)C(=O)Nc1cccc(/C=C/CNC(=O)OC(C)(C)C)c1 | US08674137B2_1551grants | 9acb41c6c1d521bf5fa5088fc3fbb13594e45e4e25f01b11963a83ed | Br[c:15]1[cH:14][cH:13][cH:12][c:11]([NH:10][C:8]([CH:4]([CH2:3][CH2:2][CH3:1])[CH2:5][CH2:6][CH3:7])=[O:9])[cH:27]1.CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CN(C)C=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.[CH2:16]=[CH:17][CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26].[Pd+2] | [CH3:1][CH2:2][CH2:3][CH:4]([CH2:5][CH2:6][CH3:7])[C:8](=[O:9])[NH:10][c:11]1[cH:12][cH:13][cH:14][c:15](/[CH:16]=[CH:17]/[CH2:18][NH:19][C:20](=[O:21])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[cH:27]1 | ([C:4]=[CH;D2;+0:5]/[c;H0;D3;+0:1](:[c:2]):[c:3])>>(Br-[c;H0;D3;+0:1](:[c:2]):[c:3]).([C:4]=[CH2;D1;+0:5]) | 0996d8c51008ea3b4ae6c7b138cc093a3a5afb04d5508cf0878c0251 | 1 | 1 | CC(=O)[O-].CC(=O)[O-].CCN(CC)CC.CN(C)C=O.Cc1ccccc1P(c1ccccc1C)c1ccccc1C.[Pd+2] | 539 |
170,985 | 599,585 | 993,167 | [NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].N12CCCN=C1CCCCC2.O>C(#N)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])=[C:14]([O:19][CH3:20])[CH:13]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2 | null | US07745641B2_1460 | 2,010 | C1CCC2=NCCCN2CC1.CC#N.Cl[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].O.[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]3[c:12]2[CH2:13][NH:14][C:15]3=[O:16])[cH:17][cH:18][c:19]1[OH:20]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]3[c:12]2[CH2:13][NH:14][C:15]3=[O:16])[cH:17][cH:18][c:19]1[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27] | 0.272111 | C1CCC2=NCCCN2CC1.CC#N.CC(C)(C)[Si](C)(C)Cl.COc1cc(-c2ccc(N)c3c2CNC3=O)ccc1O.O>>COc1cc(-c2ccc(N)c3c2CNC3=O)ccc1O[Si](C)(C)C(C)(C)C | C1CCC2=NCCCN2CC1.CC#N.CC(C)(C)[Si](C)(C)Cl.COc1cc(-c2ccc(N)c3c2CNC3=O)ccc1O.O>>COc1cc(-c2ccc(N)c3c2CNC3=O)ccc1O[Si](C)(C)C(C)(C)C | US07745641B2_1460grants | fc6ef034ed9982cff7411f36270aacdc24715fc4bab85a259b569f73 | C1CCC2=NCCCN2CC1.CC#N.Cl[Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27].O.[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]3[c:12]2[CH2:13][NH:14][C:15]3=[O:16])[cH:17][cH:18][c:19]1[OH:20] | [CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][c:9]([NH2:10])[c:11]3[c:12]2[CH2:13][NH:14][C:15]3=[O:16])[cH:17][cH:18][c:19]1[O:20][Si:21]([CH3:22])([CH3:23])[C:24]([CH3:25])([CH3:26])[CH3:27] | ([C:2]-[Si;H0;D4;+0:1](-[C;D1;H3:3])(-[C;D1;H3:4])-[O;H0;D2;+0:5]-[c:6])>>(Cl-[Si;H0;D4;+0:1](-[C:2])(-[C;D1;H3:3])-[C;D1;H3:4]).([OH;D1;+0:5]-[c:6]) | 78671a61751fb41a7735eaf781f047ef571d6531544684af2f680407 | 1 | 1 | C1CCC2=NCCCN2CC1.CC#N.O | 746 |
112,177 | 421,861 | 718,869 | [F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.ClC1C=C(N)C=CC=1SC1N(C)C=CN=1>>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([OH:11])=[CH:3][C:2]=1[F:1] | null | US07030112B2_0549 | 2,006 | Cn1ccnc1Sc1ccc(N)cc1Cl.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[F:9]>>[NH2:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[F:9] | 0.976185 | Cn1ccnc1Sc1ccc(N)cc1Cl.O=[N+]([O-])c1ccc(O)cc1F>>Nc1ccc(O)cc1F | Cn1ccnc1Sc1ccc(N)cc1Cl.O=[N+]([O-])c1ccc(O)cc1F>>Nc1ccc(O)cc1F | US07030112B2_0549grants | f7379de32acb21ab4a2ba2686f10a9dba492ef09c6ca1199f4cc861a | Cn1ccnc1Sc1ccc(N)cc1Cl.O=[N+:1]([O-])[c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[F:9] | [NH2:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[cH:7][c:8]1[F:9] | ([NH2;D1;+0:1]-[c:2])>>(O=[N+;H0;D3:1](-[O-])-[c:2]) | f0a489cd79c24ed642d5256650cdb0f98e5344b2c074824b17336ecc | 1 | 1 | Cn1ccnc1Sc1ccc(N)cc1Cl | 1 |
223,922 | 751,361 | 1,238,288 | [Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([OH:12])=O.CN(C=O)C.S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([Cl:20])=[O:12] | null | US08288397B2_0141 | 2,012 | CN(C)C=O.Cc1ccccc1.O=S(Cl)[Cl:3].O[C:2](=[O:1])[CH2:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12]>>[O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12] | 0.506727 | CN(C)C=O.Cc1ccccc1.O=C(O)Cc1c(Cl)cccc1Cl.O=S(Cl)Cl>>O=C(Cl)Cc1c(Cl)cccc1Cl | CN(C)C=O.Cc1ccccc1.O=C(O)Cc1c(Cl)cccc1Cl.O=S(Cl)Cl>>O=C(Cl)Cc1c(Cl)cccc1Cl | US08288397B2_0141grants | f17310122c92f4fba563979d6907db752d6e992d6dc0ec72f2f8a430 | CN(C)C=O.Cc1ccccc1.O=S(Cl)[Cl:3].O[C:2](=[O:1])[CH2:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12] | [O:1]=[C:2]([Cl:3])[CH2:4][c:5]1[c:6]([Cl:7])[cH:8][cH:9][cH:10][c:11]1[Cl:12] | ([C:3]-[C;H0;D3;+0:2](-[Cl;H0;D1;+0:1])=[O;D1;H0:4])>>(Cl-S(=O)-[Cl;H0;D1;+0:1]).(O-[C;H0;D3;+0:2](-[C:3])=[O;D1;H0:4]) | 876ba1f28c2f41de2ca98cf6279d2d855ebe250e1445dd0bf341762d | 1 | 1 | CN(C)C=O.Cc1ccccc1 | 53 |
252,790 | 838,248 | 1,391,784 | C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[N:14]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[CH:11][C:12](=[O:16])[N:13]([CH3:15])[N:14]=2)=[CH:5][CH:4]=1 | null | US08586588B2_0759 | 2,013 | BrB(Br)Br.C[O:9][c:8]1[cH:7][cH:6][c:5](-[c:4]2[n:3][n:2]([CH3:1])[c:14](=[O:15])[cH:13][cH:12]2)[cH:11][cH:10]1.ClCCl>>[CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]2)[cH:12][cH:13][c:14]1=[O:15] | 0.938571 | BrB(Br)Br.COc1ccc(-c2ccc(=O)n(C)n2)cc1.ClCCl>>Cn1nc(-c2ccc(O)cc2)ccc1=O | BrB(Br)Br.COc1ccc(-c2ccc(=O)n(C)n2)cc1.ClCCl>>Cn1nc(-c2ccc(O)cc2)ccc1=O | US08586588B2_0759grants | 054bb1f35c353055da7251f9e4b93bd8d17ea28464490592eb6f0978 | BrB(Br)Br.C[O:9][c:8]1[cH:7][cH:6][c:5](-[c:4]2[n:3][n:2]([CH3:1])[c:14](=[O:15])[cH:13][cH:12]2)[cH:11][cH:10]1.ClCCl | [CH3:1][n:2]1[n:3][c:4](-[c:5]2[cH:6][cH:7][c:8]([OH:9])[cH:10][cH:11]2)[cH:12][cH:13][c:14]1=[O:15] | ([OH;D1;+0:1]-[c:2])>>(C-[O;H0;D2;+0:1]-[c:2]) | f50e6edd43215fd09e75ad8277fe209f633bdb24972a58fad4063f8f | 1 | 1 | BrB(Br)Br.ClCCl | 48 |
442,826 | 1,925,004 | null | [N:1]1([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CC1C=CC(S(O[CH2:31][CH2:32][CH2:33][CH2:34][C:35]2[C:43]3[C:38](=[CH:39][CH:40]=[C:41]([F:44])[CH:42]=3)[NH:37][CH:36]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:44][C:41]1[CH:42]=[C:43]2[C:38](=[CH:39][CH:40]=1)[NH:37][CH:36]=[C:35]2[CH2:34][CH2:33][CH2:32][CH2:31][N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3=[O:19])=[CH:11][CH:12]=2)[CH2:2][CH2:3]1 | |f:2.3.4,5.6| | US20160244429A1_0350 | 2,016 | CC#N.Cc1ccc(S(=O)(=O)O[CH2:16][CH2:17][CH2:18][CH2:19][c:20]2[cH:21][nH:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]23)cc1.O=C([O-])[O-].[I-].[K+].[K+].[K+].[O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][NH:15][CH2:30][CH2:31]2)[cH:32][cH:33]1>>[O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][c:20]3[cH:21][nH:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]34)[CH2:30][CH2:31]2)[cH:32][cH:33]1 | 0.929362 | CC#N.Cc1ccc(S(=O)(=O)OCCCCc2c[nH]c3ccc(F)cc23)cc1.O=C([O-])[O-]~[K+]~[K+].O=c1ccccn1-c1ccc(N2CCNCC2)cc1.[I-]~[K+]>>O=c1ccccn1-c1ccc(N2CCN(CCCCc3c[nH]c4ccc(F)cc34)CC2)cc1 | CC#N.Cc1ccc(S(=O)(=O)OCCCCc2c[nH]c3ccc(F)cc23)cc1.O=C([O-])[O-].O=c1ccccn1-c1ccc(N2CCNCC2)cc1.[I-].[K+].[K+].[K+]>>O=c1ccccn1-c1ccc(N2CCN(CCCCc3c[nH]c4ccc(F)cc34)CC2)cc1 | US20160244429A1_0350apps | bcfc51eff8c1c569fb4a1ec7c637bc6b79f9cc77f56aad2436d7608a | CC#N.Cc1ccc(S(=O)(=O)O[CH2:16][CH2:17][CH2:18][CH2:19][c:20]2[cH:21][nH:22][c:23]3[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]23)cc1.O=C([O-])[O-].[I-].[K+].[K+].[K+].[O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][NH:15][CH2:30][CH2:31]2)[cH:32][cH:33]1 | [O:1]=[c:2]1[cH:3][cH:4][cH:5][cH:6][n:7]1-[c:8]1[cH:9][cH:10][c:11]([N:12]2[CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][c:20]3[cH:21][nH:22][c:23]4[cH:24][cH:25][c:26]([F:27])[cH:28][c:29]34)[CH2:30][CH2:31]2)[cH:32][cH:33]1 | ([C:3]-[N;H0;D3;+0:4](-[C:5])-[CH2;D2;+0:1]-[C:2])>>(C-c1:c:c:c(-S(=O)(=O)-O-[CH2;D2;+0:1]-[C:2]):c:c:1).([C:3]-[NH;D2;+0:4]-[C:5]) | 782bf8d5a2ffe41551f705ac6cb3e5edf1298a11e59e03f365b83419 | 0.5 | 2 | CC#N.O=C([O-])[O-].[I-].[K+].[K+].[K+] | 429 |
239,823 | 799,229 | 1,322,386 | [NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]([C:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:27]5[O:26][CH2:25][O:24][C:23]=5[CH:22]=[CH:21][C:20]=4[O:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=3[NH:12][CH:11]=2)=[O:9])[CH2:2]1.[CH3:33][O:34][CH2:35][C:36](Cl)=[O:37]>>[CH3:33][O:34][CH2:35][C:36]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([NH:7][C:8]([C:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([C:19]4[C:27]5[O:26][CH2:25][O:24][C:23]=5[CH:22]=[CH:21][C:20]=4[O:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:13]=3[NH:12][CH:11]=2)=[O:9])[CH2:2]1)=[O:37] | null | US08445501B2_4926 | 2,013 | Cl[C:26](=[O:27])[CH2:28][O:29][CH3:30].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([c:11]1-[c:12]1[n:13][cH:14][n:15][c:16]3[c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH2:24][NH:25][CH2:31]4)[cH:32][nH:33][c:34]13)[O:35][CH2:36][O:37]2>>[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([c:11]1-[c:12]1[n:13][cH:14][n:15][c:16]3[c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][O:29][CH3:30])[CH2:31]4)[cH:32][nH:33][c:34]13)[O:35][CH2:36][O:37]2 | 0.984326 | CCCCOc1ccc2c(c1-c1ncnc3c(C(=O)NC4CCCNC4)c[nH]c13)OCO2.COCC(=O)Cl>>CCCCOc1ccc2c(c1-c1ncnc3c(C(=O)NC4CCCN(C(=O)COC)C4)c[nH]c13)OCO2 | CCCCOc1ccc2c(c1-c1ncnc3c(C(=O)NC4CCCNC4)c[nH]c13)OCO2.COCC(=O)Cl>>CCCCOc1ccc2c(c1-c1ncnc3c(C(=O)NC4CCCN(C(=O)COC)C4)c[nH]c13)OCO2 | US08445501B2_4926grants | 0a3fe3788315c693aa70cad420dff234973362db7c6a3d95d3317bfd | Cl[C:26](=[O:27])[CH2:28][O:29][CH3:30].[CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([c:11]1-[c:12]1[n:13][cH:14][n:15][c:16]3[c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH2:24][NH:25][CH2:31]4)[cH:32][nH:33][c:34]13)[O:35][CH2:36][O:37]2 | [CH3:1][CH2:2][CH2:3][CH2:4][O:5][c:6]1[cH:7][cH:8][c:9]2[c:10]([c:11]1-[c:12]1[n:13][cH:14][n:15][c:16]3[c:17]([C:18](=[O:19])[NH:20][CH:21]4[CH2:22][CH2:23][CH2:24][N:25]([C:26](=[O:27])[CH2:28][O:29][CH3:30])[CH2:31]4)[cH:32][nH:33][c:34]13)[O:35][CH2:36][O:37]2 | ([C:4]-[N;H0;D3;+0:5](-[C:6])-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3])>>(Cl-[C;H0;D3;+0:1](-[C:2])=[O;D1;H0:3]).([C:4]-[NH;D2;+0:5]-[C:6]) | 58bfc612ddb3c3923670b0fade9423da56792769e45e6b088debac9e | 1 | 1 | null | 125 |