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

Participants

Reaction Steps

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%.

Provenance & Evidence