Cyclohexanecarboxaldehyde → HCID 57012568, compound

Participants

Reaction Steps

5-(Adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c and d with the modification that norbornadiene-7-carboxaldehyde (J. Stapersma and G. W. Klumpp Tetrahedron, 1981, 37, 187) was used in step d instead of cyclohexanecarboxaldehyde. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the resulting 5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole-4-carboxylic acid was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 20, step d to afford 3-{[5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.1]hepta-2,5-dien-7-yl-1H-imidazole-4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the crude product was purified by flash column chromatography (silica, DCM/methanol 95:5 ) to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.10 (1H, br s), 9.65 (1H, br s), 8.42 (1H, br s), 7.92 (1H, d), 7.62 (1H, d), 7.41 (1H, t), 6.90 (2H, s), 6.59 (2H, s), 4.75 (2H, s), 4.06 (2H, s), 3.47 (1H, s), 2.10 (3H, br s), 1.75 (6H, s), 1.58 (6H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 58.71; H, 7.44; N, 7.50%. C36H48N4O9.3.0 mols H2O requires: C, 58.84; H, 7.41; N, 7.62%.

Provenance & Evidence