(Diethylamino)sulfur trifluoride → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-fluoropropyl)-1H-1,2,3-triazole-4-carboxamide

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Reaction Steps

To a solution of N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-(3-hydroxypropyl)-1H-1,2,3-triazole-4-carboxamide (0.40 g) obtained in Example 113 in dichloromethane (4.5 ml) was added diethylaminosulfur trifluoride (0.18 ml) at −78° C. The reaction mixture was stirred for 5 hr while gradually heating to room temperature. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column (hexane/ethyl acetate=6/4 to ethyl acetate). The resultant product was recrystallized from ethyl acetate/hexane to give the title compound as a colorless powder (0.024 g, 6%).

Provenance & Evidence