Triethylamine → N-cyclopropyl-3-(difluoromethyl)-1-methyl-N-{1-[methyl(phenyl)-amino]propan-2-yl}-1H-pyrazole-4-carboxamide

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Reaction Steps

At ambient temperature, a solution of 220 mg (1.13 mmol) of 3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride in 1 ml of tetrahydrofurane is added dropwise to a solution of 210 mg (1.03 mmol) of N2-cyclopropyl-N1-methyl-N1-phenylpropane-1,2-diamine and 0.16 ml (1.13 mmol) of triethylamine in 5 ml of tetrahydrofurane. The reaction mixture is stirred for 15 hrs at room temperature. The solvent to is removed under vacuum and 100 ml of water are then added to the residue. The watery layer is extracted twice with ethyl acetate (2×150 ml) and the combined organic layers are successively washed by a 1 N solution of HCl, a saturated solution of potassium carbonate and brine and filtered over a ChemElut cartridge to yield after concentration 180 mg of a brown oil. Column chromatography (gradient heptane/ethyl acetate) yielded 150 mg (38% yield) of N-cyclopropyl-3-(difluoromethyl)-1-methyl-N-{1-[methyl(phenyl)-amino]propan-2-yl}-1H-pyrazole-4-carboxamide as a yellow oil (M+H=363).

Provenance & Evidence