Ammonium Chloride → HCID 66777194, compound

Participants

Reaction Steps

To a mixture of 6-{[cyclohexyl(5-fluoro-3-methyl-1-benzofuran-2-yl)methyl]amino}pyridine-3-carboxylic acid (294 mg) synthesized in Example A51(4), ethyl 3-(methylamino)propanoate (151 mg), 1-hydroxybenzotriazole monohydrate (176 mg), triethylamine (322 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (221 mg), and the mixture was stirred at room temperature overnight. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30-70% ethyl acetate/hexane) to give the title object compound (236 mg, 62%) as a pale-brown solid.

Provenance & Evidence