Cesium carbonate → HCID 86587528, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-ethyl-4-nitro-1H-pyrazole-5-carboxamide (8.20 g, 44.6 mmol, prepared using procedure in WO9849166), tert-butyl (2S)-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1-pyrrolidinecarboxylate (17.4 g, 49.0 mmol, prepared using procedure in WO9926944) and cesium carbonate (16.0 g, 49.2 mmol) in N,N-dimethylformamide (100 ml) was stirred at 20° C. for 4 days and then at 50° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc (300 ml) and water (300 ml). The phases were separated, and the aqueous layer extracted with further EtOAc (2×200 ml). The organic phases were combined, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was partially purified by column chromatography (DCM/MeOH, 100:0-91:9) and then the regioisomers were separated by further column chromatography (Et2O/EtOAc, 100:0-50:50) to afford the title compound of preparation 34 (1.23 g, 3.35 mmol, 7.5%); mp 68-75° C.

Provenance & Evidence