Sodium hydride → Cyclopropanesulfonic acid {6-chloro-3,3-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carbonyl}-amide

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Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (114 mg, 2.8 mmol) in N,N-dimethylformamide (1.5 mL) was added cyclopropanesulfonamide (350 mg, 2.9 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 6-chloro-3,3-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (120 mg, 0.3 mmol) and 1,1′-carbonyldiimidazole (118 mg, 0.8 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 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 {6-chloro-3,3-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carbonyl}-amide (62 mg, 40%) as a white solid: LC/MS m/e calcd for C26H33ClN4O3S (M+H)+: 517.0, observed: 517.1.

Provenance & Evidence