Sodium hydride → HCID 58476191, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methanesulfonamide (237 mg, 2.5 mmol) in N,N-dimethylformamide (1.5 mL) was added sodium hydride (100 mg, 2.48 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 3,3-dimethyl-2-(3-phenylcarbamoyl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (200 mg, 0.5 mmol) and 1,1′-carbonyldiimidazole (162 mg, 1 mmol) in N,N-dimethylformamide (1 mL) was stirred at 70° C. for 1 h. Then the above suspension of methanesulfonamide 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 3-(6-methanesulfonylaminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-N-phenyl-benzamide (100 mg, 18%) as a white solid: LC/MS m/e calcd for C26H27N3O4S (M+H)+: 478.59, observed: 478.2.

Provenance & Evidence