3-Aminobenzenesulfonic acid → HCID 18405376, compound

Participants

Reaction Steps

Oxalyl chloride (147 μl, 1.69 mmol) was added to an ice cooled suspension of 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) (500 mg, 1.40 mmol) in DCM (8 ml), followed by two drops of DMF. The mixture was stirred at room temperature for 1 h, then the solvent was evaporated. The residue was susupended in THF (8 ml), and tretaed sequentially with metanilic acid (346 mg, 2.00 mmol), N,N-diisopropylethylamine (348 μl, 2.00 mmol) and 4-dimethylaminopyridine (DMAP) (cat). The suspension was stirred at room temperature for 120 h. Water (30 ml), ethyl acetate (30 ml) and methanol (2 ml) were added and the mixture was stirred for 1 h. The solid was filtered and dried to afford the title compound (294 mg, 41%). 1H NMR (300 MHz, d6-DMSO) 10.10 (1H, br s), 7.92 (1H, br s), 7.67 (1H, m), 7.34 (2H, m), 2.98-2.86 (3H, m), 2.02-1.34 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 57.87; H, 7.73; N, 7.74%. C35H54N5O9S.1.0 mol H2O requires: C, 57.99; H, 7.79; N, 7.73%.

Provenance & Evidence