4-Methylmorpholine → 5-[[(4-Fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-N,N,4-trimethylpyridine-2-carboxamide

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Reaction Steps

To a solution of 5-[[(4-fluorophenyl)thio](2,3,6-trifluorophenyl)methyl]-4-m ethylpyridine-2-carboxylic acid (383 mg, 0.94 mmol) in methylene chloride (10 ml), dimethylamine hydrochloride (85 mg, 1.03 mmol), 1-hydroxybenzotriazole (140 mg, 1.03 mmol), 4-methylmorpholine (0.227 ml, 2.07 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (198 mg, 1.03 mmol) were added at room temperature. After stirring for 17 hours at room temperature, the reaction mixture was washed with 0.5 N hydrochloric acid. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=1:1 was concentrated under reduced pressure to obtain the title compound (373 mg, 0.86 mmol, 91%) as a white solid.

Provenance & Evidence