Water → HCID 18405528, compound

Participants

Reaction Steps

To a suspension of 3-{[5-(2-adamantan-1-yl-ethyl)-2-(1-methoxymethyl-cyclohexyl)-1H-imidazole-4-carbonyl]-amino}-benzoic acid (Example 203) (300 mg, 0.58 mmol) in DCM (10 ml) was added 1 M solution of boron tribromide in DCM (1.72 ml, 1.72 mmol) at 0° C. The mixture was stirred at room temperature for 16 h, cooled to 0° C., and water (20 ml) was added slowly. The product was extracted with DCM/MeOH (3×20 ml of 9:1 mixture), the organic phase was dried (MgSO4) and the solvent was evaporated. The crude product was purified by flash column chromatography (silica, DCM/MeOH, 95:5) to afford the title compound as a white solid (40.5 mg, 14%). 1H NMR (300 MHz, d6-DMSO) 9.51 (1H, s), 8.38 (1H, s), 7.92 (1H, d), 7.60 (1H, d), 7.40 (1H, t), 3.41 (2H, s), 2.87 (2H, m), 2.05 (2H, m), 1.94 (3H, br s), 1.65 (6H, m), 1.52 (11H, m), 1.34 (5H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.86; H, 8.33; N, 7.76%. C37H56N4O9.1.6 H2O requires: C, 60.86; H, 8.18; N, 7.67%.

Provenance & Evidence