5-(2-Adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carboxylic acid → 5-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acid benzyl ester

HRID 1018340Notes

Reaction equation

HRID 1018340 reaction equation
[C:1]12([CH2:11][CH2:12][C:13]3[NH:17][C:16]([C:18]4[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=4[CH3:24])=[N:15][C:14]=3[C:27](O)=[O:28])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:30]([O:37][C:38](=[O:47])[C:39]1[CH:44]=[C:43]([NH2:45])[CH:42]=[CH:41][C:40]=1[CH3:46])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>>[CH2:30]([O:37][C:38](=[O:47])[C:39]1[CH:44]=[C:43]([NH:45][C:27]([C:14]2[N:15]=[C:16]([C:18]3[C:19]([CH3:26])=[N:20][C:21]([CH3:25])=[CH:22][C:23]=3[CH3:24])[NH:17][C:13]=2[CH2:12][CH2:11][C:1]23[CH2:2][CH:3]4[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]4)[CH2:8]2)[CH2:10]3)=[O:28])[CH:42]=[CH:41][C:40]=1[CH3:46])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

3

Reactant 2

HCID 184056735-(2-Adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carboxylic acidHCID 538373385-Amino-2-methyl-benzoic acid benzyl ester

Product 1

HCID 696867185-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-2-methyl-benzoic acid benzyl ester

Procedure

5-(2-Adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carboxylic acid (Example 182) was reacted with 5-amino-2-methyl-benzoic acid benzyl ester according to the procedure of Example 20, step d to afford 5-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-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) 12.40 (1H, br s), 9.69 (1H, s), 8.30 (1H, d), 7.76 (1H, d), 7.17 (1H, d), 7.05 (1H, s), 2.99 (2H, m), 2.44 (3H, s), 2.43 (3H, s), 2.25 (3H, s), 2.09 (3H, s), 1.92 (3H, br s), 1.64 (6H, m), 1.51 (6H, br s), 1.42 (2H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 54.92; H, 8.21; N, 8.30%. C39H55N5O8.7.0 mols H2O requires: C, 55.24; H, 8.20; N, 8.26%.

Sources & evidence

ORD record
ord-dedc0b04fc5c4df3a400d2f77f233913
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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