Cyanoacetamide → benzyl 4-(5-amino-4-carbamoyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Participants

Reaction Steps

To a stirred solution of 2-Cyanoacetamide (520 mg, 6.19 mmol) in EtOH (8.6 mL) at room temperature was added Sodium ethoxide (21% in EtOH, 1.6 mL, 4.13 mmol). A solution of 111 (842 mg, 2.063 mmol) in EtOH (1.7 mL) was added dropwise and the resulting suspension was allowed to stir for 10 min at room temperature, then for 2 h at 80° C. The solvent was removed and after the usual work-up the crude material was purified via Biotage (10% to 40% EtOAc/Hexane; 25S column) to give 117 (327 mg, 38.5% yield) as an orange solid. LRMS (ESI): calc.411.4; found 412.1 (MH)+.

Provenance & Evidence