Sodium hydride → HCID 58476197, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methanesulfonic acid amide (266 mg, 2.8 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (112 mg, 2.8 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-fluoro-5-(4-isopropyl-piperazin-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (120 mg, 0.28 mmol), and 1,1′-carbonyldiimidazole (91.5 mg, 0.56 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h. The above suspension of methanesulfonic acid amide and sodium hydride in N,N-dimethylformamide was added and the mixture was allowed to stir at 25° C. for 1 h. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded N-{2-[3-Fluoro-5-(4-isopropyl-piperazin-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}methanesulfonamide (20 mg, 14%) as a white solid: LC/MS m/e calcd for C26H35FN4O3S (M+H)+: 503.7, observed: 503.3.

Provenance & Evidence