4-Methylmorpholine → HCID 59750942, compound

Participants

Reaction Steps

To a dichloromethane (6 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 N-methylmorpholine (77.7 μl, 0.708 mmol), O-methylhydroxylamine hydrochloride (23.6 mg, 0.283 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (54.3 mg, 0.283 mmol). The resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added tetrahydrofuran (1 ml). After stirring at room temperature for 18 hours, the reaction mixture was diluted with dichloromethane. The diluted mixture was washed with water and brine. The organic layer thus obtained was dried over magnesium sulfate and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated to give a white solid. The resulting solid was washed with ethyl acetate to give the title compound (55.1 mg, 0.122 mmol, 52%) as a white powder.

Provenance & Evidence