N,O-Dimethylhydroxylamine → HCID 86624858, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-benzoic acid (4.2 g) in DMF (25 mL) and carbonyldiimide (2.4 g) was stirred at 60° C. for 30 min, and N-methoxy-N-methylamine (1.41 g) was added. The mixture was stirred at 80° C. for 16 h, then the volatiles evaporated, and the residue partitioned between EtOAc and H2O, then between EtOAc and HCl (0.1 N aq). The organic phase was adsorbed on silica gel and chromatographed. Chromatography on silica (80 g) against hexane/EtOAc (100:0 to 50:50) provided 4-chloro-2-[6-(2,5-dimethyl-pyrrol-1-yl)-pyridin-2-ylamino]-N-methoxy-N-methyl-benzamide (˜1.6 g).

Provenance & Evidence