4-Methylmorpholine → HCID 57736419, compound

Participants

Reaction Steps

To a solution of 5-[(2,5-difluorophenyl)[(4-fluorophenyl)sulfonyl]methyl]-4-methylpyridine-2-carboxylic acid (93 mg, 0.221 mmol) obtained in Example 12 in methylene chloride (3 ml), 2-amino-1,3-propanediol (24 mg, 0.265 mmol), 1-hydroxybenzotriazole (30 mg, 0.221 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (51 mg, 0.265 mmol) and 4-methylmorpholine (29 μl, 0.265 mmol) were added, and the resulting mixture was stirred for 17 hours at room temperature. Ethyl acetate was added to the reaction solution, and the mixture was washed sequentially with a saturated solution of sodium hydrogencarbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting concentration residue was subjected to silica gel column chromatography, and the fraction obtained from an elution with methanol:methylene chloride (=1:20) was concentrated under reduced pressure. Ethylacetate-hexane was added to the resulting concentration residue, and the solid thus precipitated was collected by filtration, to obtain the title compound (81 mg, 0.164 mmol, 74%) as a white powder.

Provenance & Evidence