Dimethylformamide → HCID 66778108, compound

Participants

Reaction Steps

To a mixture of 4-({cyclohexyl[5-fluoro-3-(methoxymethyl)-1-benzofuran-2-yl]methyl}amino)benzoic acid (200 mg) synthesized in Example A47(7), ethyl 3-(methylamino)propanoate (95.6 mg), 1-hydroxybenzotriazole monohydrate (112 mg), triethylamine (203 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (140 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 (197 mg, 77%) as a pale-yellow oil.

Provenance & Evidence