Water → HCID 67381022, compound

HRID 1804268Notes

Reaction equation

HRID 1804268 reaction equation
[O:1]1[CH2:5][CH2:4][NH:3][C:2]1=[O:6].[H-].[Na+].[Br:9][C:10]1[CH:11]=[C:12]([CH3:32])[C:13]([N:16]2[CH2:21][CH2:20][N:19]([C:22]([C:24]3[CH:25]=[N:26][C:27](F)=[CH:28][C:29]=3[CH3:30])=[O:23])[CH2:18][CH2:17]2)=[N:14][CH:15]=1.O>CN(C=O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH3:32])[C:13]([N:16]2[CH2:17][CH2:18][N:19]([C:22]([C:24]3[C:29]([CH3:30])=[CH:28][C:27]([N:3]4[CH2:4][CH2:5][O:1][C:2]4=[O:6])=[N:26][CH:25]=3)=[O:23])[CH2:20][CH2:21]2)=[N:14][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 739492-OxazolidinoneHCID 58484740HCID 58484740, compound

Product 1

HCID 67381022HCID 67381022, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of oxazolidin-2-one (174 mg) in DMF (4 mL) was added sodium hydride (80 mg) at 10° C., and the mixture was stirred for 30 min. Furthermore, [4-(5-bromo-3-methylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (590 mg) described in Preparation Example 113 was added, and the mixture was stirred at 80° C. for 5 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate) to give 3-{5-[4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}oxazolidin-2-one (423 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 80° C. for 5 hr
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2cd9cd07fe314d9aac8f2596367c42b2
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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