(1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride → methyl 4-(3-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)ureido)-2-fluorobenzoate

Participants

Reaction Steps

To a stirred solution of (1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methanamine hydrochloride (321 mg, 1.03 mmol, 1.0 eq) in DCM (10 mL) was added TEA (0.28 mL, 0.26 mmol, 2.0 eq) followed by methyl 2-fluoro-4-(phenoxycarbonylamino)benzoate (300 mg, 1.03 mmol, 1.0 eq) at RT and stirred for 16 h. Then the reaction mixture was evaporated, diluted with water (50 mL) and extracted with ethyl acetate (2×70 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and evaporated under vacuum. The crude product was purified CC using EtOAc/PE (2:3) as eluent to obtain methyl 4-(3-((1-(3-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methyl)ureido)-2-fluorobenzoate (300 mg; 63%) as a white solid (TLC: EtOAc/PE (1:1); Rf: 0.3).

Provenance & Evidence