Triethylamine → HCID 178523782, compound

Participants

Reaction Steps

cis-4-Amino-cyclohexanecarboxylic acid benzyl ester mesylate (5.34 g, 13.2 mmol) was dissolved in dimethylformamide (75 ml) and triethylamine (5.5 ml, 39.5 mmol) was added followed by 5-fluoro-2-chloronicotinic acid (2.31 g, 13.2 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.77 g, 14.5 mmol) and 1-hydroxybenzotriazole (1.96 g, 14.5 mmol). The reaction was stirred under nitrogen at room temperature for 18 h and the solvent was removed under reduced pressure. The residue was partitioned between sat. sodium bicarbonate solution (50 ml) and ethyl acetate (75 ml) and the aqueous phase was extracted with ethyl acetate (2×75 ml). The combined organic extracts were washed with water (2×20 ml), brine (20 ml), dried over MgSO4 and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate:pentane (1:1, by volume) to give cis-4-[(2-Chloro-5-fluoro-pyridine-3-carbonyl)-amino]-cyclohexanecarboxylic acid benzyl ester (2.14 g) as a white solid.

Provenance & Evidence