4-Methylmorpholine → HCID 23114700, compound

Participants

Reaction Steps

To a dichloromethane (4 ml) suspension of the [6-[(4-chlorophenylsulfonyl)(2,5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (100 mg, 0.236 mmol) obtained in Example 50 were added thionyl chloride (1.00 ml) and N,N-dimethylformamide (one drop). The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated to dryness and the residue thus obtained was dissolved in dichloromethane (6 ml). To the resulting solution were added N-methylmorpholine (51.8 μl, 0.472 mmol) and 4-methylcyclohexylamine (37.4 μl, 0.283 mmol). The resulting mixture was stirred at room temperature for 18 hours, followed by dilution with dichloromethane. The diluted mixture was washed sequentially with 1N hydrochloric acid, water and brine, dried over magnesium sulfate and concentrated. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated to give a white solid. The solid thus obtained was recrystallized from ethyl acetate-hexane to give the title compound (70.3 mg, 0.135 mmol, 57%) as a white powder.

Provenance & Evidence