Methyl 5-amino-2-fluorobenzoate → 5-{[5-(2-adamantan-1-yl-ethyl)-2-(2,4,6-trimethyl-pyridine-3-yl)-1H-imidazole-4-carbonyl]-amino}-2-fluoro-benzoic acid methyl 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-fluoro-benzoic acid methyl 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-fluoro-benzoic acid methyl ester. The ester was hydrolysed following the procedure of Example 36, step d, to afford the title compound as a white solid. 1H NMR (300 MHz, d6-DMSO) 12.50 (1H, br s), 9.67 (1H, s), 8.15 (1H, d), 7.71 (1H, m), 7.03 (2H, m), 2.99 (2H, m), 2.42 (3H, s), 2.25 (3H, s), 2.09 (3H, s), 1.92 (3H, br s), 1.60 (6H, m), 1.50 (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, 53.44; H, 7.81; N, 8.03%. C38H52FN5O8.7.0 mols H2O requires: C, 53.57; H, 7.81; N, 8.22%.

Provenance & Evidence