Hydrochloric Acid → 5-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl 4-methylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A mixed liquid comprising 2.0 g of N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-3-hydroxy-4,5-dihydro-1H-pyrazole-5-carboxamide and 41 ml of N,N-dimethylformamide was cooled to 0° C., and 0.2 g of sodium hydride (60% oil suspension) was added. After stirring for one hour, 1.2 g of p-toluenesulfonyl chloride was added at 0° C. After stirring for 1.5 hours, the reaction liquid was poured to 120 ml of a 1 M HCl aqueous solution, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1) to obtain 2.45 g of the desired product in the form of a paste.

Provenance & Evidence