Methyl iodide → HCID 178487292, compound

HRID 538053Notes

Reaction equation

HRID 538053 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[NH:12][C:11](=[O:13])[N:10]([CH2:14][C@H:15]3[CH2:20][CH2:19][C@H:18]([C:21]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:29]=1.[CH3:30]I>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]2[N:12]([CH3:30])[C:11](=[O:13])[N:10]([CH2:14][C@H:15]3[CH2:20][CH2:19][C@H:18]([C:21]([N:23]4[CH2:24][CH2:25][O:26][CH2:27][CH2:28]4)=[O:22])[CH2:17][CH2:16]3)[C:9]=2[CH:29]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178488109HCID 178488109, compound

Product 1

HCID 178487292HCID 178487292, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in mineral oil, 12 mg, 0.3 mmol) was added to a solution of 6-Methoxy-1-[trans-4-(morpholine-4-carbonyl)-cyclohexylmethyl]-1,3-dihydro-benzoimidazol-2-one (56 mg, 0.15 mmol) in DMF (1.5 ml). MeI (19 μL, 0.3 mmol) was added and the mixture was stirred at room temperature for six hours. The solvent was evaporated, the crude was dissolved in 2 ml of DCM and the solution was washed with H2O. The organic layer was separated and the solvent was removed under reduced pressure. The crude material was purified by column chromatography with EtAc/MeOH (9/1) as eluent. 45 mg (yield 78%) of the title compound were isolated.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude was dissolved in 2 ml of DCM
  3. washthe solution was washed with H2O
  4. customThe organic layer was separated
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was purified by column chromatography with EtAc/MeOH (9/1) as eluent

Sources & evidence

ORD record
ord-cc36800b5e7f47c2bf92efff21e275ab
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

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