1-Methylpiperazine → HCID 86757740, compound

Participants

Reaction Steps

To a solution of 200 mg of (Z)-[4,4-difluoro-1-(1-phenyl-5-trifluoromethyl-1H-pyrazole-4-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepin-5-ylidene]acetic acid in 20 ml of tetrahydrofuran were added 90 mg of 1-hydroxybenzotriazole, 130 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide monohydrochloride and 60 mg of 1-methylpiperazine, and the mixture was stirred at room temperature for 18 hours. A saturated aqueous solution of sodium bicarbonate was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with a saturated aqueous solution of NaCl and dried over magnesium sulfate, followed by evaporating off the solvent. The residue was purified by silica gel column chromatography (eluting with chloroform-methanol). The resulting residue (190 mg) was dissolved in 5 ml of chloroform, and 0.5 ml of a 4N HCl/ethyl acetate solution was added thereto, followed by stirring at room temperature. The solvent was evaporated off, and the residue was crystallized from ethanol-diethyl ether to give 190 mg of (Z)-4,4-difluoro-5-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]-1-(1-phenyl-5-trifluoromethyl-1H-pyrazole-4-carbonyl)-2,3,4,5-tetrahydro-1H-1-benzoazepine monohydrochloride as a colorless powder.

Provenance & Evidence