Sodium hydride → HCID 59054202, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (70 mg, 1.75 mmol) in N,N-dimethylformamide (3 mL) was added methanesulfonamide (166 mg, 1.75 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h to afford Solution A26. A solution of 2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.25 mmol) and 1,1′-carbonyldiimidazole (81 mg, 0.5 mmol) in N,N-dimethylformamide (2 mL) was stirred at 70° C. for 1 h and cooled to room temperature to afford Solution B26. Solution B26 was added to Solution A26 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 N-{2-[2-chloro-5-(2-oxo-oxazolidin-3-yl)-phenyl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-methanesulfonamide (13 mg, 11%) as a white solid: MS (ESI) M+1=478.0.

Provenance & Evidence