Acetonitrile → 2,2-Dimethylpropyl 4-{4-[5-(methylthio)-1,2,4-oxadiazol-3-yl]pyridin-2-yl}-1-piperazinecarboxylate

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Reaction Steps

2,2-Dimethylpropyl 4-{4-[amino(hydroxyimino)methyl]pyridin-2-yl}piperazine-1-carboxylate (340 mg) obtained in Example 26-1) was dissolved in acetonitrile (2 mL), and 1,1′-thiocarbonyldiimidazole (231 mg) was added thereto and stirred at room temperature for 2 hours. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was dissolved in dimethylformamide (2 mL), and methyl iodide (0.080 mL) and potassium carbonate (198 mg) were added thereto and stirred at room temperature for 1 hour. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=7/3) to obtain 25.2 mg of the entitled compound as a colorless oil.

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