4-Methylmorpholine → HCID 23114700, compound

Participants

Reaction Steps

Thionyl chloride (1.00 ml) and N,N-dimethylformamide (one drop) were added to a suspension of the [6-[(4-chlorophenylsulfonyl)(2, 5-difluorophenyl)methyl]pyridin-3-yl]carboxylic acid (100 ing, 0.236 minol), which had been obtained in Example 338, in dichloromethane (4 ml). The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was concentrated to dryness. The residue was then dissolved in dichioromethane (6 ml), followed by the addition of N-methylmorpholine (51.8 μl, 0.472 mmol) and 4-methylcyclohexylamine (37.4 μl, 0.283 mmol). After the reaction mixture was stirred at room temperature for 18 hours, the mixture was diluted with dichloromethane. The solution was washed successively with 1N hydrochloric acid, water and brine, dried over magnesium sulfate and concentrated. The residue was subjected to flash chromatography on a silica gel column. A fraction obtained from the elution portion with hexane:ethyl acetate=3:1 was concentrated, whereby a white solid was obtained. The resulting solid was recrystallized from ethyl acetate-hexane, whereby the title compound (70.3 mg, 0.135 mmol, 57%) was obtained as a white powder.

Provenance & Evidence