Methyl iodide → HCID 18331427, compound

HRID 2270544Notes

Reaction equation

HRID 2270544 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.CI.[H-].[Na+].[C:35](=O)([O-])O.[Na+]>C(OCC)(=O)C.CN(C)C=O>[CH3:35][NH:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 18331432HCID 18331432, compound

Product 1

HCID 18331427HCID 18331427, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of the compound (88.5 mg) obtained in Example 3, methyl iodide (15 μl) and dimethylformamide (2 ml), sodium hydride (content=60%; 10 mg) was added and the resulting mixture was stirred at room temperature for 4 days. To the reaction mixture, ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:3) to give 19.3 mg of the titled compound (yield, 21%).

Workup

  1. additionwas added
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-9c4b86a92b7e4db0a59f7ba5d307eba8
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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