Sodium hydride → HCID 53492111, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (745 mg, 18.6 mmol) in N,N-dimethylformamide (2.5 mL) was added ethanesulfonamide (2.3 g, 19 mmol) at room temperature. 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 (690 mg, 1.9 mmol) and 1,1′-carbonyldiimidazole (650 mg, 3.8 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 70° C. After stirring at 70° C. for 1 h, the above suspension of ethanesulfonamide 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 ethanesulfonic acid [3,3-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (347 mg, 40%) as a white solid: LC/MS m/e calcd for C24H31N3O4S (M+H)+: 458.61, observed: 458.0.

Provenance & Evidence