2-Methylbenzenesulfonamide → HCID 15872196, compound

Participants

Reaction Steps

To a solution of 4-[1-(benzhydryl-carbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.50 grams, 0.81 mmol), 4-dimethylaminopyridine (0.015 grams, 1.21 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (0.23 g, 1.21 mmol) in methylene chloride (30 mL) was added o-tolylsulfonamide (0.14 g, 0.81 mmol). The resulting solution was stirred for 12 hours at room temperature. The solution was diluted with methylene chloride and washed with 1 M hydrochloric acid (aq). The organics were dried over magnesium sulfate and concentrated. Chromatography on silica gel (2% methanol/methylene chloride), followed by recrystallization from wet ether gave the titled compound (0.455 grams, 73% yield). m.p.=253-254° C. Anal. calcd. for C44H42N4O7S: C, 68.55; H, 5.49; N, 7.27. Found: C, 69.21; H, 5.54; N, 7.14. HRMS calcd. for C44H42N4O7S: 770.2774. Found 770.2736.

Provenance & Evidence