Ammonium Chloride → HCID 66778769, compound

Participants

Reaction Steps

To a mixture of 5-{[cyclohexyl(3-methyl-1-benzothiophen-2-yl)methyl]amino}pyridine-2-carboxylic acid (247 mg) synthesized in Example A59(2), β-alanine ethyl ester hydrochloride (149 mg), 1-hydroxybenzotriazole monohydrate (149 mg), triethylamine (270 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (186 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 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 (274 mg, 88%) as a colorless oil.

Provenance & Evidence