Water → HCID 178501109, compound

HRID 538056Notes

Reaction equation

HRID 538056 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([F:24])([F:23])[F:22])[CH:19]=[CH:20][C:15]=3[NH:14][C:13]2=[O:25])[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[CH3:28]I.O>CN(C=O)C>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21]([F:24])([F:22])[F:23])[CH:19]=[CH:20][C:15]=3[N:14]([CH3:28])[C:13]2=[O:25])[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178501111HCID 178501111, compound

Product 1

HCID 178501109HCID 178501109, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

trans-4-(2-Oxo-6-trifluoromethyl-2,3-dihydro-benzoimidazol-1-ylmethyl)-cyclohexanecarboxylic acid methyl ester (0.87 mg, 2.44 mmol) was dissolved in anhydrous DMF. NaH (1.95 g, 4.9 mmol, 60% in mineral oil) and MeI (0.30 ml, 4.9 mmol) were added and the mixture was stirred at room temperature for two days. H2O was added and the solvents were evaporated. The crude was dissolved in DCM (15 ml) and washed with H2O (10 ml). The organic layer was dried over Na2SO4, filtered and the solvent removed to give 0.93 g (yield quantitative) of the titled compound.

Workup

  1. customthe solvents were evaporated
  2. dissolutionThe crude was dissolved in DCM (15 ml)
  3. washwashed with H2O (10 ml)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give

Sources & evidence

ORD record
ord-c59d553109d449b0b1caef23518bb00f
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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