Triethylamine → 5-Amino-1-(4-fluorophenyl)-N-(3,3,3-trifluoro-2-{[(2-fluoroethyl)amino]methyl}-2-hydroxypropyl)-1H-pyrazole-4-carboxamide

Participants

Reaction Steps

To a solution of 5-amino-1-(4-fluorophenyl)-N-{[2-(trifluoromethyl)-2-oxiranyl]methyl}-1H-pyrazole-4-carboxamide (1.03 g, 3 mmol) in anhydrous acetonitrile (10 ml) was added 2-fluoroethylamine hydrochloride (650 mg, 6 mmol, ca. 90% purity) and triethylamine (0.98 ml, 7 mmol) and the resulting suspension was shaken for 4 days. It was partitioned between ethyl acetate (70 ml) and water (20 ml), washed with saturated brine (20 ml), dried over sodium sulphate and evaporated to give a gum (1.57 g). This was purified on 100 g SiO2 using the Flashmaster 2 with 0-100°/0 ethyl acetate in cyclohexane 60 minute gradient as eluent. This gave the title compound (924 mg).

Provenance & Evidence