Sodium hydride → HCID 68172328, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (448 mg, 11.2 mmol) in N,N-dimethylformamide (3 mL) was added cyclopropanesulfonic acid amide (1.35 g, 11.2 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A51. A solution of 4,4-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (564 mg, 1.5 mmol) and 1,1′-carbonyldiimidazole (519 mg, 3.2 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B51. Solution B51 was added to Solution A51 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 {4,4-dimethyl-2-[3-(4-methyl-piperazin-1-yl)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (140 mg, 10%) as a white solid: MS (ESI) M+1=483.3.

Provenance & Evidence