Ammonium Chloride → HCID 57736411, compound

Participants

Reaction Steps

To a solution 4-methyl-5-[[[6-(trifluoromethyl)pyridin-3-yl]sulfonyl](2,3,6-trifluorophenyl)methyl]pyridine-2-carboxylic acid (392 mg, 0.800 mmol) in N,N-dimethylformamide (10 ml), (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (624 mg, 1.20 mmol), benzotriazol-1-ol (162 mg, 1.20 mmol), ammonium chloride (85.6 mg, 1.60 mmol), and N-ethyldiisopropylamine (0.557 ml, 3.20 mmol) were added in a nitrogen atmosphere at room temperature. After stirring for 2 hours at the same temperature, the reaction mixture was dissolved in ethyl acetate, and the solution was washed with 1 N hydrochloric acid, 1 N aqueous sodium hydroxide, saturated aqueous ammonium chloride, and then saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained 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, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and then was collected by filtration, to obtain the title compound (229 mg, 0.468 mmol, 58%) as a white solid. The filtrate was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol and diethyl ether, and then was collected by filtration, to obtain the title compound (66 mg, 0.135 mmol, 17%) as a white solid.

Provenance & Evidence