Sodium hydride → HCID 58476201, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (149 mg, 3.7 mmol) in N,N-dimethylformamide (2.5 mL) was added cyclopropanesulfonamide (460 mg, 3.8 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-(2,6-dimethyl-morpholin-4-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (150 mg, 0.38 mmol) and 1,1′-carbonyldiimidazole (125 mg, 0.76 mmol) in N,N-dimethylformamide (1.0 mL) was stirred at 70° C. After stirring at 70° C. for 1 h, the above suspension of cyclopropanesulfonamide 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-(2,6-dimethyl-morpholin-4-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (56 mg, 30%) as a white solid: LC/MS m/e calcd for C27H35N3O4S (M+H)+: 498.66, observed: 498.0.

Provenance & Evidence