N-methyl-2-pyrrolidone → HCID 57721329, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-chloro-N-(2,4-difluorophenyl)nicotinamide (126 mg, 0.51 mmol) and 4-(4-amino-2-fluorophenoxy)picolinamide (172 mg, 0.49 mmol, Compound C of Example 3) in 3 mL of NMP was added toluenesulfonic acid monohydrate (71 mg, 0.37 mmol). The mixture was stirred at 120° C. for 2 h and at 160° C. for 15 h. The solution was cooled to rt and purified on preparative (RP) HPLC. The fractions containing the desired product pooled and concentrated in vacuo. The residue was then partitioned between 1N NaOH and EtOAc and the two layers were separated. The organic layer washed with brine and dried over MgSO4. After filtration and concentration, the desired product was obtained (30 mg, 11% yield). MS (ESI+) m/z 558.22, 560.22 (M+H)+.

Provenance & Evidence