Water → 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-N-pyridazin-3-ylpiperazine-1-carboxamide

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Reaction Conditions

Reaction Steps

A mixture of 2,2,2-trichloroethyl pyridazin-3-ylcarbamate (226 mg, 0.835 mmol), 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine (200 mg, 0.760 mmol) and diisopropylethylamine (0.265 ml, 1.52 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 3 days. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by high performance liquid chromatography (YMC HPLC column; Solution A: 0.1% trifluoroacetic acid solution in acetonitrile; Solution B: 0.1% aqueous trifluoroacetic acid solution; eluted with 10% Solution A to 100% Solution A), and a saturated aqueous sodium hydrogen carbonate solution was added. The mixture was extracted with ethyl acetate. The extract was washed with water and dried over magnesium sulfate anhydrous, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the desired product (32.3 mg, 11.1%) as a solid.

Provenance & Evidence