Dimethylformamide → HCID 86752549, compound

Participants

Reaction Steps

A mixture of 1-(4-chlorophenyl)-3-(4-pyridyl)-5-hydroxy pyrazole (406 mg; 1.49 mmol) and Cs2CO3 (243 mg; 0.75 mmol) in methanol (8 ml) was stirred at room temperature for 4 hours. The solvent was concentrated in vacuo, and the residue was dried in vacuo overnight. To the above residue was added 7 ml of DMF and 2-bromomethyl-4-isopropyl-6-methoxy-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (519 mg, 1.49 mmol) and the resulting mixture was stirred at room temperature for 5 hours and poured into water. The above mixture was extracted with methylene chloride (3×), the organic layer was dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (silica gel; 33-50% ethyl acetate/hexane; 12-50% methylene chloride/acetone) and recrystallized from methylene chloride/hexane to afford 401 mg (50%) of 4-isopropyl-6-methoxy-2-[1-(4-chlorophenyl)-3-(4-pyridyl) pyrazol-5-yl-oxymethyl]-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (Formula I: R1 =4-Cl--Ph; R2 =4-pyridyl; R3 =H; R4 =CH(CH3)2 ; R5 =6-OCH3) as a white solid, m.p. >190° C. (dec.).

Provenance & Evidence