Ammonium Chloride → Ethyl 3-{[(4-{[cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate

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To a mixture of 4-{[cyclohexyl(3-methylthieno[2,3-c]pyridin-2-yl)methyl]amino}benzoic acid (202 mg) synthesized above, ethyl 3-(methylamino)propanoate (104 mg), 1-hydroxybenzotriazole monohydrate (122 mg), triethylamine (222 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (152 mg), and the mixture was stirred at room temperature for 1 day. 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 (30-100% ethyl acetate/hexane, then 0-10% methanol/acetic acid) to give the title object compound (151 mg, 58%) as a pale-yellow oil.

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