Methyl iodide → HCID 74221696, compound

HRID 931007Notes

Reaction equation

HRID 931007 reaction equation
[O:1]1[C:5]([C:6]2[C:7]3[N:8]([C:16]([C:19]([NH:21][CH:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:20])=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)=[CH:4][N:3]=[CH:2]1.I[CH3:29].[H-].[Na+].[Cl-].[NH4+]>CN(C=O)C>[CH3:29][N:21]([CH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)[C:19]([C:16]1[N:8]2[CH:9]=[C:10]([C:12]([F:14])([F:15])[F:13])[CH:11]=[C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)[C:7]2=[N:18][CH:17]=1)=[O:20]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 118378880HCID 118378880, compound

Product 1

HCID 74221696HCID 74221696, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 8-(1,3-oxazol-5-yl)-N-(tetrahydro-2H-pyran-4-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxamide (55 mg) and iodomethane (18 μL) in DMF (2 mL) was added 60% sodium hydride (8.7 mg), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (47 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-a729ea4dfa514dbfb32f2dc1829bc278
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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