Ammonium Chloride → Ethyl 3-{[(4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}phenyl)carbonyl](methyl)amino}propanoate

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Reaction Steps

To a mixture of 4-{[2-ethyl-1-(3-methyl-1-benzothiophen-2-yl)butyl]amino}benzoic acid (250 mg) synthesized in Example A134(3), ethyl 3-(methylamino)propanoate (134 mg), 1-hydroxybenzotriazole monohydrate (156 mg), triethylamine (284 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (196 mg), and the mixture was stirred at room temperature 2.5 days. 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 and saturated aqueous sodium hydrogen carbonate solution, 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 (253 mg, 77%) as a colorless oil.

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