Water → 2-(3-Benzyl-4-chloro-2-oxo-2,3-dihydroimidazo[4.5-c]pyridin-1-ylmethyl)benzonitrile

HRID 2112914Notes

Reaction equation

HRID 2112914 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7]([N:14]1[C:18]2[C:19]([Cl:23])=[N:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(O[CH2:29][CH3:30])(=O)C.O>CN(C)C=O>[CH2:7]([N:14]1[C:18]2[C:19]([Cl:23])=[N:20][CH:21]=[CH:22][C:17]=2[N:16]([CH2:15][C:30]2[CH:29]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]#[N:14])[C:1]1=[O:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 230705823-Benzyl-4-chloro-1,3-dihydroimidazo[4,5-c]pyridin-2-one

Product 1

HCID 230853512-(3-Benzyl-4-chloro-2-oxo-2,3-dihydroimidazo[4.5-c]pyridin-1-ylmethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (0.152 g) and (2-bromomethyl)benzonitrile (0.216 g) were added to a solution of 3-benzyl-4-chloro1,3-dihydroimidazo[4.5-c]pyridin-2-one (0.259 g) in N,N-dimethylformamide (5 mL). This was stirred at room temperature for 16 hours. Ethyl acetate (60 mL) and water (30 mL) were added, and the organic layer was washed twice with 30 mL of water and once with 30 mL of saturated aqueous sodium chloride solution. This was then dried over anhydrous magnesium sulfate. The organic layer was filtered and concentrated under reduced pressure, and the residue was then purified by silica gel chromatography. The ethyl acetate:hexane 3:2 fraction gave the title compound (0.364 g).

Workup

  1. washthe organic layer was washed twice with 30 mL of water and once with 30 mL of saturated aqueous sodium chloride solution
  2. dry with materialThis was then dried over anhydrous magnesium sulfate
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was then purified by silica gel chromatography

Sources & evidence

ORD record
ord-600dbcc97c15488b93e71f260487cd64
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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