2-Pyridinecarboxaldehyde → 3-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester
Reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=4)=[N:15][C:14]=3[C:24](O)=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N1C=CC=CC=1C=O.[CH2:35]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([NH2:50])[CH:45]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43](=[O:51])[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([NH:50][C:24]([C:14]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:10][CH:5]4[CH2:4][CH:3]([CH2:9][CH:7]([CH2:6]4)[CH2:8]2)[CH2:2]3)=[O:25])[CH:45]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1Participants
Procedure
5-(2-Adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carboxylic acid (prepared according to the procedure of Example 70, steps a and b, with the modification that pyridine-2-carboxaldehyde was used instead of 2-dimethylamino-benzaldehyde in step a) was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 177, step a to afford 3-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl group was removed following the procedure of Example 1, step e, to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 13.18 (1H, br s), 9.84 (1H, br s), 8.63 (1H, d), 8.48 (1H, s), 8.23 (1H, d), 8.00 (1H, d), 7.93 (1H, td), 7.63 (1H, d), 7.42 (2H, m), 2.99 (2H, m), 1.95 (3H, br s), 1.65 (6H, m), 1.54 (6H, s), 1.42 (2H, m). The product was converted to the L-tartaric acid salt and lyophilised from water/dioxan. Found: C, 58.35; H, 6.11; N, 8.80%. C32H36N4O9.2.0 mols H2O requires: C, 58.23; H, 6.14; N, 8.53%.
Sources & evidence
- ORD record
- ord-9474266ef9f94db2ab51b6f885291546
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479531B1
Reaction notes
Loading…