Water → HCID 67380925, compound

HRID 1804269Notes

Reaction equation

HRID 1804269 reaction equation
[CH3:1][C@@H:2]1[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[H-].[Na+].[Br:10][C:11]1[CH:12]=[C:13]([CH3:33])[C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[CH:26]=[N:27][C:28](F)=[CH:29][C:30]=3[CH3:31])=[O:24])[CH2:19][CH2:18]2)=[N:15][CH:16]=1.O>CN(C=O)C>[Br:10][C:11]1[CH:12]=[C:13]([CH3:33])[C:14]([N:17]2[CH2:18][CH2:19][N:20]([C:23]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([N:3]4[C@H:2]([CH3:1])[CH2:6][O:5][C:4]4=[O:7])=[N:27][CH:26]=3)=[O:24])[CH2:21][CH2:22]2)=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 58484740HCID 58484740, compound

Product 1

HCID 67380925HCID 67380925, compoundYield 48.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-4-methyloxazolidin-2-one (222 mg) described in Preparation Example 25 in DMF (4 mL) was added sodium hydride (84 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 (447 mg) described in Preparation Example 113 was added, and the mixture was stirred at 80° C. for 3 hr and at 100° C. for 3 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 (R)-3-{5-[4-(5-bromo-3-methylpyridin-2-yl)piperazine-1-carbonyl]-4-methylpyridin-2-yl}-4-methyloxazolidin-2-one (260 mg).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred at 80° C. for 3 hr and at 100° C. for 3 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-812136c024ac4a65a095d88089ef4ad7
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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