Sodium hydride → HCID 59053630, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of cyclopropanesulfonic acid amide (1.1 g, 9.1 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (361 mg, 9 mmol). The resulting mixture was stirred at 25° C. for 1 h to afford Solution A63. A solution of 6-chloro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (520 mg, 1.3 mmol) and 1,1′-carbonyldiimidazole (422 mg, 2.6 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B63. Solution B63 was added to Solution A63 and the resulting mixture was stirred at 25° C. for 1 h. To the reaction mixture was added water (0.5 mL). The mixture was filtered to remove the insoluble solid, and the filtrate was purified 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 [6-chloro-4,4-dimethyl-2-(3-morpholin-4-yl-phenyl)-1,2,3,4-tetrahydro-quinoline-8-carbonyl]-amide (25 mg, 4%) as a white solid: MS (ESI) M+1=504.2.

Provenance & Evidence