Cesium carbonate → HCID 22648218, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (20.0 g, 109 mmol, prepared using procedure in WO9849166), 4-(2-chloroethyl)morpholine hydrochloride (22.2 g, 120 mmol), K2CO3 (29.9 g, 217 mmol) and cesium carbonate (7.08 g, 21.7 mmol) in N,N-dimethylformamide (100 ml) was stirred at 55° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc (350 ml) and water (500 ml). The phases were separated, and the aqueous layer extracted with further EtOAc (150 ml). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/MeOH, 100:0-80:20, followed by EtOAc/MeOH/NH3, 80:20:1) to afford the title compound of preparation 21 (16.21 g, 54.5 mmol, 50%); mp 132-133° C.

Provenance & Evidence