Triethylamine → HCID 69144872, compound

Participants

Reaction Steps

To a solution of [1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetic acid (synthesized in Preparation Example 3B-1) (678 mg) in dichloromethane (15 mL) was added N,N-dimethylformamide (2 drops) dropwise. Oxalyl chloride (228 mg) was then added to the solution under ice cooling. The solution was stirred under ice cooling for 2 hours. A 5-mL aliquot of the reaction solution was taken and was added to a solution of methyl anthranilate (99 mg) and triethylamine (182 mg) in dichloromethane (15 mL) dropwise under ice cooling. The reaction solution was stirred for 18 hours while the temperature was allowed to rise to room temperature. NH Silica gel was then added to the reaction solution, and it was concentrated under reduced pressure. The residue was purified by chromatography [silica gel, chloroform-methanol (20:1)] to give methyl 2-[2-[1-[2-[4-[N-(p-tolyl)-2-furancarboxamido]piperidin-1-yl]ethyl]cyclohexyl]acetylamino]benzoate (150 mg).

Provenance & Evidence