Sodium hydride → HCID 53492376, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of cyclopropanesulfonic acid amide (182 mg, 1.5 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (57 mg, 1.43 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 6-chloro-3,3-dimethyl-2-{3-[(pyrazine-2-carbonyl)-amino]-phenyl}-1,2,3,4-tetrahydro-quinoline-8-carboxylic acid (65 mg, 0.15 mmol) and 1,1′-carbonyldiimidazole (49 mg, 0.3 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 70° C. for 1 h, 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 pyrazine-2-carboxylic acid [3-(6-chloro-8-cyclopropanesulfonylaminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-amide (40 mg, 49%) as a white solid: LC/MS m/e calcd for C26H26ClN5O4S (M+H)+: 541.05, observed: 540.0.

Provenance & Evidence