Methyl iodide → HCID 57584174, compound

HRID 910617Notes

Reaction equation

HRID 910617 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:9]([C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][CH:11]=2)=[CH:8][CH:7]=[CH:6][N:5]1[CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]1.CI.[C:31](=O)([O-])O.[Na+]>O.CN(C)C=O>[CH3:31][N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][N:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:18][CH:19]=3)[C:4]2=[O:3])[CH2:23][C:24]1=[O:28]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57583914HCID 57583914, compound

Product 1

HCID 57584174HCID 57584174, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

With cooling with ice, sodium hydride (60% oil suspension, 50 mg) was added to an N,N-dimethylformamide (10 ml) solution of methyl 4-{2-oxo-1-[2-(3-oxopiperazin-1-yl)ethyl]-1,2-dihydropyridin-3-yl}benzoate (380 mg), followed by stirring for 5 minutes, and then methyl iodide (70 μl) was added. With cooling with ice, the reaction mixture was stirred for 1.5 hours. Water with ice (20 ml) and aqueous saturated sodium hydrogencarbonate solution (10 ml) were added to the reaction mixture, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate, then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5) to obtain methyl 4-{1-[2-(4-methyl-3-oxopiperazin-1-yl)ethyl]-2-oxo-1,2-dihydropyridin-3-yl}benzoate (350 mg) as a pale yellow oil.

Workup

  1. temperatureWith cooling with ice
  2. stirringthe reaction mixture was stirred for 1.5 hours
  3. extractionfollowed by extraction with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-93b29bdadd9e4d65b9a377633ecf7a44
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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