1-Hydroxybenzotriazole → 4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

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Reaction Steps

A mixture of 7-methoxy-3-methyl-1H-indole-2-carboxylic acid (61 mg, 0.3 mmol), 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (83 mg, 0.3 mmol), N-hydroxybenzotriazole (61 mg, 0.45 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (86 mg, 0.45 mmol) in 1:1 dichloromethane/dimethylformamide was stirred at room temperature for overnight. After the reaction, solvent was concentrated. The resulted mixture was mixed with water and extracted with ethyl acetate twice. The organic layers were collected, combined, washed with brine before being dried over sodium sulfate, and then concentrated to give a solid. The crude product was purified by flash chromatography (Merck silica gel 60, 230-400 mesh, 0%-100% ethyl acetate in hexane) to give 40 mg of 4-{4-[(7-methoxy-3-methyl-1H-indole-2-carbonyl)-amino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester as an off-white solid. LCMS calcd for C26H32N4O4 (m/e) 464, obsd 465 (M+H).

Provenance & Evidence