Sodium hydride → HCID 53492447, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methanesulfonamide (4.75 g, 50 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (1.98 g, 49.5 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (3.66 g, 10 mmol) and 1,1′-carbonyldiimidazole (3.24 g, 20 mmol) in N,N-dimethylformamide (7 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 N-[3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (0.99 g, 22%) as a white solid: LC/MS m/e calcd for C23H29N3O4S (M+H)+: 444.57, observed: 444.1.

Provenance & Evidence