Methyl iodide → HCID 46916727, compound

HRID 467960Notes

Reaction equation

HRID 467960 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:25])[F:24])[CH:17]=2)[C:8]([C:10]2[N:14]=[CH:13][NH:12][N:11]=2)=[O:9])[CH2:3][CH2:2]1.[H-].[Na+].CI.[C:31](=O)([O-])O.[Na+]>CN(C=O)C>[CH3:31][N:12]1[CH:13]=[N:14][C:10]([C:8]([N:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]([F:26])([F:24])[F:25])[CH:17]=2)=[O:9])=[N:11]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178520000HCID 178520000, compound

Product 1

HCID 46916727HCID 46916727, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tetrahydro-2H-pyran-4-yl)-N-[3-(trifluoromethoxy)benzyl]-1H-1,2,4-triazole-3-carboxamide (138 mg) in DMF (2 mL), sodium hydride (60%, 18 mg) was added and the resulting mixture was stirred for 10 minutes; thereafter, methyl iodide (35 μL) was added and the resulting mixture was stirred overnight at room temperature. To the reaction mixture, a saturated aqueous solution of sodium hydrogencarbonate was added and extraction was conducted with ethyl acetate. The ethyl acetate layer was washed with saturated saline and dried over anhydrous magnesium sulfate. After filtering off the desiccant, the filtrate was concentrated under reduced pressure and the resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=1:0 to 1:3) to give the titled compound (75 mg).

Workup

  1. stirringthe resulting mixture was stirred overnight at room temperature
  2. extractionextraction
  3. washThe ethyl acetate layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtering off the desiccant
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by column chromatography (NH silica gel cartridge; hexane/ethyl acetate=1:0 to 1:3)

Sources & evidence

ORD record
ord-e46b2be82ef443e5837d69353cedf036
Source dataset
uspto-grants-2014_01
Patent number
US08623898B2

Reaction notes

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