Cesium carbonate → HCID 23503220, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (15.7 g, 85.6 mmol, prepared using procedure in WO9849166), 3-(chloromethyl)pyridazine (11.0 g, 85.6 mmol, prepared using procedure in WO0023449) and cesium carbonate (27.8 g, 85.6 mmol) in N,N-dimethylformamide (200 ml) was stirred at 20° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between DCM (200 ml) and 10% aqueous Na2CO3 (100 ml). The phases were separated, and the aqueous layer extracted with further DCM (6×50 ml). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc/MeOH, 95:5-9010) to afford the title compound of preparation 43 (Note, the regioisomers were assigned on the basis of nOe experiments) (4.09 g, 14.8 mmol, 17%):

Provenance & Evidence