Sodium hydride → HCID 58476265, compound

HRID 1801167Notes

Reaction equation

HRID 1801167 reaction equation
[H-].[Na+].[CH3:3][S:4]([NH2:7])(=[O:6])=[O:5].[CH:8]([C@@H:11]1[CH2:15][O:14][C:13](=[O:16])[N:12]1[C:17]1[CH:18]=[C:19]([CH:23]2[C:32]([CH3:34])([CH3:33])[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:35](O)=[O:36])[CH:29]=3)[NH:24]2)[CH:20]=[CH:21][CH:22]=1)([CH3:10])[CH3:9].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[CH:8]([C@@H:11]1[CH2:15][O:14][C:13](=[O:16])[N:12]1[C:17]1[CH:18]=[C:19]([CH:23]2[C:32]([CH3:34])([CH3:33])[CH2:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([C:35]([NH:7][S:4]([CH3:3])(=[O:6])=[O:5])=[O:36])[CH:29]=3)[NH:24]2)[CH:20]=[CH:21][CH:22]=1)([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 72879Methanesulfonamide2×HCID 58476162HCID 58476162, compound

Product 1

HCID 58476265HCID 58476265, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (290 mg, 7.3 mmol) in N,N-dimethylformamide (2.5 mL) was added methanesulfonamide (703 mg, 7.4 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-((R)-4-isopropyl-2-oxo-oxazolidin-3-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (300 mg, 0.74 mmol) and 1,1′-carbonyldiimidazole (300 mg, 1.84 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 methanesulfonamide 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 N-{2-[3-((R)-4-isopropyl-2-oxo-oxazolidin-3-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-methanesulfonamide (71 mg, 20%) as a white solid: LC/MS m/e calcd for C25H31N3O5S (M+H)+: 486.61, observed: 486.1.

Workup

  1. stirringAfter stirring at 70° C. for 1 h
  2. additionwas added
  3. stirringto stir at 25° C. for 1 h
  4. customPurification 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)

Sources & evidence

ORD record
ord-f2c77d194064465caded71fd34158fb0
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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