Methyl iodide → HCID 22319025, compound

HRID 229701Notes

Reaction equation

HRID 229701 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:30])[N:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:12]=[C:13]([C:15]2[NH:16][C:17]3[CH:22]=[CH:21][N:20]=[CH:19][C:18]=3[N:23]=2)[CH:14]=1)#[N:2].[CH3:31]I>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:30])[N:11]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:12]=[C:13]([C:15]2[N:16]=[C:19]3[N:20]([CH3:31])[CH:21]=[CH:22][CH:17]=[C:18]3[N:23]=2)[CH:14]=1)#[N:2]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178509647HCID 178509647, compound

Product 1

HCID 22319025HCID 22319025, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3 mg of 3-(2-cyanophenyl)-5-(1H-imidazo[4,5-c]pyridin-2-yl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 3 ml of acetone. To the mixture was added 2 ml of methyl iodide, followed by stirring at room temperature overnight. The mixture was evaporated, and the residue was diluted with 1 ml of water. To the mixture was added 20 mg of sodium hydroxide, followed by stirring at room temperature for 4 hours. The reaction solution was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was evaporated, and the residue was purified by silica gel chromatography (NH silica) (hexane/ethyl acetate system), to give 2 mg of the title compound.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was diluted with 1 ml of water
  3. additionTo the mixture was added 20 mg of sodium hydroxide
  4. stirringby stirring at room temperature for 4 hours
  5. extractionThe reaction solution was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customThe filtrate was evaporated
  10. customthe residue was purified by silica gel chromatography (NH silica) (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-8920a6bc9ecf46339662e6a3aa28bde0
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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