Dimethylcarbamoyl Chloride → 4-[1-(dimethylcarbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid

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Reaction Conditions

Reaction Steps

To a slurry of sodium hydride (60% by wt in mineral oil, 0.037 grams, 0.77 mmol) in dimethylformamide (5 mL), at 0° C., was added a solution of 4-[5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.15 grams, 0.37 mmol) in dimethylformamide (5 mL). The resulting solution was stirred at 0° C. for 20 minutes, then dimethylcarbamoyl chloride (0.071 mL, 0.77 mmol) was added. The solution was warmed to room temperature and stirred for 1 hour. The reaction was quenched by addition of 1 M sodium hydroxide (aq), and the mixture was extracted with ethyl acetate. The combined organics were washed with 1 M hydrochloric acid (aq) and set aside. The aqueous phase was made acidic with 1 M hydrochloric acid (aq) and extracted with ethyl acetate. All the organics were combined and dried over magnesium sulfate and concentrated. Chromatography on silica gel (2% methanol/methylene chloride) gave 4-[1-(dimethylcarbamoyl)-5-(cyclopentyloxycarbonyl)amino-1H-indol-3-ylmethyl]-3-methoxy-benzoic acid (0.16 grams, 89% yield).

Provenance & Evidence