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

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To a mixture of 4-{[cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methyl]amino}benzoic acid (330 mg) synthesized above, β-alanine ethyl ester hydrochloride (209 mg), 1-hydroxybenzotriazole monohydrate (208 mg), triethylamine (379 μL) and N,N-dimethylformamide (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (261 mg), and the mixture was stirred overnight at room temperature. 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 (70% ethyl acetate/hexane) to give the title object compound (383 mg, 91%) as a pale-brown oil

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