Dimethylformamide → HCID 86658609, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methanesulfonamide (158 mg, 1.66 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (66 mg, 1.66 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-(1-isopropylcarbamoyl-1-methyl-ethylamino)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.236 mmol) and 1,1′-carbonyldiimidazole (77 mg, 0.473 mmol) in N,N-dimethylformamide (1.5 mL) was stirred at 70° C. for 1 h. Then the above suspension of methanesulfonamide and sodium hydride in N,N-dimethylformamide was added and the mixture was allowed to stir at 25° C. for 12 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 N-isopropyl-2-[3-(6-methanesulfonyl aminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionamide (25 mg, 21%) as a white solid: LC/MS m/e calcd for C26H36N4O4S (M+H)+: 501.67, observed: 501.1.

Provenance & Evidence