Water → HCID 71252548, compound

HRID 2411693Notes

Reaction equation

HRID 2411693 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[H-].[Na+].[CH3:9][C:10]1[C:11]([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:12][CH:13]=[C:14]([CH3:16])[CH:15]=1.O>CN(C)C=O>[CH3:9][C:10]1[C:11]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[C:30]([CH3:31])=[CH:29][C:28]([N:1]4[CH2:5][CH2:4][CH2:3][C:2]4=[O:6])=[N:27][CH:26]=3)=[O:24])[CH2:19][CH2:18]2)=[N:12][CH:13]=[C:14]([CH3:16])[CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 120252-PyrrolidoneHCID 24758Sodium hydrideHCID 71252935HCID 71252935, compound

Product 1

HCID 71252548HCID 71252548, compoundYield 16.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Pyrrolidin-2-one (322 mg) was dissolved in N,N-dimethylformamide (4 mL), sodium hydride (159 mg) was added, and the mixture was stirred for 30 min. To the reaction mixture was further added [4-(3,5-dimethylpyridin-2-yl)piperazin-1-yl](6-fluoro-4-methylpyridin-3-yl)methanone (620 mg) described in Preparation Example 146, and the mixture was stirred at 100° C. for 5 hr. The reaction mixture was cooled, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and the solvent was evaporated. The obtained residue was purified by column chromatography (hexane:ethyl acetate) to give the title compound (125 mg).

Workup

  1. customdescribed in Preparation Example 146
  2. stirringthe mixture was stirred at 100° C. for 5 hr
  3. temperatureThe reaction mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by column chromatography (hexane:ethyl acetate)

Sources & evidence

ORD record
ord-bcef774f16754b5a9ac4954bde6576a6
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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