Methyl iodide → HCID 23090169, compound

HRID 1437306Notes

Reaction equation

HRID 1437306 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]([N:24]3[CH2:28][CH2:27][C:26](=[O:29])[NH:25]3)=[O:23])=[N:12]2)=[CH:7][CH:6]=1.CI.[C:32](=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:3][O:4][C:5]1[N:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)=[CH:14][C:13]([C:22]([N:24]3[CH2:28][CH2:27][C:26](=[O:29])[N:25]3[CH3:32])=[O:23])=[N:12]2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 23090244HCID 23090244, compound

Product 1

HCID 23090169HCID 23090169, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% Sodium hydride (142.4 mg) was added to the above-obtained 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]-3-oxopyrazolidine (0.542 g) in N,N-dimethylformamide (5 mL) at room temperature, followed by stirring for 15 minutes. Subsequently, methyl iodide (0.828 mL) was added to the resultant mixture, followed by stirring for 10 days. Potassium carbonate (0.614 g) and methyl iodide (0.276 mL) were added to the reaction mixture. The resultant mixture was stirred at 60° C. for 2 hours, and then cooled in air. The reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate. The mixture was subjected to filtration, and the solvent was removed under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate-hexane), to thereby give the title compound as a solid (89.8 mg, 15%).

Workup

  1. stirringby stirring for 10 days
  2. temperaturecooled in air
  3. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate solution and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  5. filtrationThe mixture was subjected to filtration
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-07adde5d949e4dae8090cb95e137f98c
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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