Methyl iodide → HCID 23090118, compound

HRID 1437301Notes

Reaction equation

HRID 1437301 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[CH2:30][CH2:29][C:28](=[O:31])[NH:27][CH2:26][CH2:25]3)=[O:23])=[N:12]2)=[CH:7][CH:6]=1.[CH3:32]I>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[CH2:30][CH2:29][C:28](=[O:31])[N:27]([CH3:32])[CH2:26][CH2:25]3)=[O:23])=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 23090472HCID 23090472, compound

Product 1

HCID 23090118HCID 23090118, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C., the sodium hydride (washed with pentan and dried, 20.4 mg) was added to a solution of 1-[1-(6-methoxy-3-pyridyl)-5-(2-pyridyl)pyrazole-3-carbonyl]-5-oxo-1,4-diazepane (0.253 g) obtained in Example 108 in N,N-dimethylformamide (5.0 mL), and the mixture was stirred for 15 minutes. To the reaction mixture, methyl iodide (0.0602 mL) was added, and the mixture was stirred at room temperature for 14 hours. The resultant mixture was partitioned between water and chloroform-methanol (5%). The aqueous layer was further extracted with chloroform-methanol (5%), and the organic layers were combined, followed by washing with saturated brine and drying over sodium sulfate anhydrate. After filtration, the solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (chloroform-methanol), to thereby give the title compound as an amorphous product (0.231 g, 88%).

Workup

  1. stirringthe mixture was stirred at room temperature for 14 hours
  2. customThe resultant mixture was partitioned between water and chloroform-methanol (5%)
  3. extractionThe aqueous layer was further extracted with chloroform-methanol (5%)
  4. washby washing with saturated brine
  5. dry with materialdrying over sodium sulfate anhydrate
  6. filtrationAfter filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified through silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-3b6ef1cc99364699b9d9465a19981ceb
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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