Hydrochloric Acid → Ethyl 3-{[(4-{[cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}phenyl)carbonyl](methyl)amino}propanoate

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To a mixture of 4-{[cyclohexyl(3-methyl-5-nitro-1-benzofuran-2-yl)methyl]amino}benzoic acid (1.54 g) synthesized above, ethyl 3-(methylamino)propanoate (593 mg), 1-hydroxybenzotriazole monohydrate (692 mg), triethylamine (1.26 mL) and N,N-dimethylformamide (15 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (867 mg), and the mixture was stirred overnight at room temperature. 1N Hydrochloric acid was added to quench the reaction, and the 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 (50% ethyl acetate/hexane) to give the title object compound (1.41 g, 72%) as a yellow solid.

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