Water → HCID 66668631, compound

HRID 1617631Notes

Reaction equation

HRID 1617631 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14](=[O:17])[NH:15][CH:16]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24](=O)([O-])[O-].[K+].[K+].IC.O>CN(C)C(=O)C>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][C:9]([C:11]2[CH:12]=[CH:13][C:14](=[O:17])[N:15]([CH3:24])[CH:16]=2)=[O:10])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 66668615HCID 66668615, compound

Product 1

HCID 66668631HCID 66668631, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 5-(3,3-diphenyl-propionyl)-1H-pyridin-2-one (60 mg, example 160, step 5) in N,N-dimethylacetamide (1 ml) were added powdered potassium carbonate (30 mg) and iodomethane (30 mg). The mixture was stirred at room temperature for 5.5 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 85:15) to give the title compound (54 mg) as a colorless solid, MS (ESI+): m/z=318.2 [M+H]+.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe product was purified by chromatography (SiO2, dichloromethane/methanol 1:0 to 85:15)

Sources & evidence

ORD record
ord-520e4d87ba4141378606c2a8a746b63a
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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