Sodium hydride → HCID 53492705, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of cyclopropanesulfonic acid amide (650 mg, 5.36 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (210 mg, 5.36 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (210 mg, 0.67 mmol) and 1,1′-carbonyldiimidazole (220 mg, 1.34 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h. Then the above suspension of cyclopropanesulfonic 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 cyclopropanesulfonic acid [2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (40 mg, 15%) as a white solid: LC/MS m/e calcd for C21H22F2N2O3S (M+H)+: 421.5, observed: 421.2.

Provenance & Evidence