Ethyl Acetate → HCID 23085260, compound

HRID 2112921Notes

Reaction equation

HRID 2112921 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]#[C:10][CH3:11].[Cl:12][C:13]1[C:18]2[NH:19][C:20](=[O:23])[N:21]([CH3:22])[C:17]=2[CH:16]=[CH:15][N:14]=1.C(OCC)(=O)C>CN(C)C=O.O>[CH2:8]([N:19]1[C:18]2[C:13]([Cl:12])=[N:14][CH:15]=[CH:16][C:17]=2[N:21]([CH3:22])[C:20]1=[O:23])[C:9]#[C:10][CH3:11]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 9113604-chloro-1-methyl-1,3-dihydroimidazo[4.5-c]pyridin-2-oneHCID 27568621-Bromo-2-butyne

Product 1

HCID 23085260HCID 23085260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (1.17 g) and 1-bromo-2-butyne (0.742 mL) were added to a solution of 4-chloro-1-methyl-1,3-dihydroimidazo[4.5-c]pyridin-2-one in N,N-dimethylformamide (50 mL). This was then stirred at room temperature for 16 hours. Ethyl acetate (300 mL) and water (200 mL) were added, and the organic layer was washed twice with 200 mL of water and then once with 200 mL of saturated aqueous sodium chloride solution, then was dried over anhydrous magnesium sulfate. The organic layer was filtered and concentrated under reduced pressure, and the residue was purified by silica gel chromatography. The ethyl acetate:hexane 3:2 fraction gave the title compound (0.980 g).

Workup

  1. washthe organic layer was washed twice with 200 mL of water
  2. dry with materialonce with 200 mL of saturated aqueous sodium chloride solution, then was dried over anhydrous magnesium sulfate
  3. filtrationThe organic layer was filtered
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c099edf6602e489380382fc3ec5ad804
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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