2-Pyridinecarboxaldehyde → 5-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acid benzyl ester

HRID 1018338Notes

Reaction equation

HRID 1018338 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:52])[C:44]1[CH:49]=[C:48]([NH2:50])[CH:47]=[CH:46][C:45]=1[CH3:51])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[CH2:35]([O:42][C:43](=[O:52])[C:44]1[CH:49]=[C:48]([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:47]=[CH:46][C:45]=1[CH3:51])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 142732-PyridinecarboxaldehydeHCID 184055755-(2-Adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carboxylic acidHCID 538373385-Amino-2-methyl-benzoic acid benzyl ester

Product 1

HCID 569776175-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acid benzyl ester

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 5-amino-2-methyl-benzoic acid benzyl ester according to the procedure of Example 177, step a to afford 5-{[5-(2-adamantan-1-yl-ethyl)-2-pyridine-2-yl-1H-imidazole-4-carbonyl]-amino}-2-methyl-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), 9.71 (1H, br s), 8.66 (1H, d), 8.32 (1H, s), 8.25 (1H, d), 7.96 (1H, td), 7.86 (1H, dd), 7.44 (1H, m), 7.24 (1H, d), 2.98 (2H, m), 2.48 (3H, s),1.94 (3H, br s), 1.63 (6H, m), 1.53 (6H, m), 1.42 (2H, m). The product was converted to the L-tartaric acid salt and lyophilised from water/dioxan. Found: C, 59.07; H, 6.40; N, 8.28%. C33H38N4O8.2.0 mols H2O requires: C, 59.10; H, 6.31; N, 8.35%.

Sources & evidence

ORD record
ord-e8f6b7fdda8b4dfb86f9197a48b126e6
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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