Water → HCID 57855775, compound

HRID 475594Notes

Reaction equation

HRID 475594 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:14]3[O:15][CH:16]=[C:17]([CH2:19][NH:20][C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:30])[F:29])[N:18]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1.[H-].[Na+].[CH3:35]I.O>CN(C)C=O.C(OCC)(=O)C>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([C:14]3[O:15][CH:16]=[C:17]([CH2:19][N:20]([CH3:35])[C:21](=[O:32])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]([F:31])([F:29])[F:30])[N:18]=3)[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68983952HCID 68983952, compound

Product 1

HCID 57855775HCID 57855775, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[2-(3-cyclopropylmethoxy-4-methoxyphenyl)oxazol-4-ylmethyl]-2-trifluoromethylbenzamide obtained in Example 25 was dissolved in 1 ml of dimethylformamide. A 30 mg quantity of sodium hydride was added thereto with ice-cooling and stirring, and the mixture was stirred for 30 minutes. A 30 mg quantity of methyl iodide was added thereto, and the reaction mixture was stirred at room temperature for 2 hours. Water and ethyl acetate were then added thereto, and extraction was performed. The organic layer was washed with water twice and concentrated by removing the solvent under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1) to give 35 mg of colorless oily N-[2-(3-cyclopropylmethoxy-4-methoxyphenyl)oxazol-4-ylmethyl]-N-methyl-2-trifluoromethylbenzamide.

Workup

  1. temperaturewith ice-cooling
  2. stirringthe mixture was stirred for 30 minutes
  3. stirringthe reaction mixture was stirred at room temperature for 2 hours
  4. extractionextraction
  5. washThe organic layer was washed with water twice
  6. concentrationconcentrated
  7. customby removing the solvent under reduced pressure
  8. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c3b3f4e41cec43538f6dba2a794b950e
Source dataset
uspto-grants-2014_01
Patent number
US08637559B2

Reaction notes

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