Methyl iodide → HCID 121386252, compound

HRID 2202960Notes

Reaction equation

HRID 2202960 reaction equation
IC.[Cl:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[C:22]([CH:24]5[CH2:26][CH:25]5[C:27]([OH:29])=[O:28])[N:21]([CH3:30])[C:20]=4[CH:31]=3)[C:12](=[O:32])[CH:11]=2)=[CH:6][CH:5]=1.[C:35](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]([C:16]3[CH:17]=[CH:18][C:19]4[N:23]=[C:22]([CH:24]5[CH2:26][CH:25]5[C:27]([O:29][CH3:35])=[O:28])[N:21]([CH3:30])[C:20]=4[CH:31]=3)[C:12](=[O:32])[CH:11]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 89691090HCID 89691090, compound

Product 1

HCID 121386252HCID 121386252, compoundYield 49.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodomethane (0.111 ml) was added to a solution of (1RS,2SR)-2-(6-(4-((4-chlorobenzyl)oxy)-2-oxopyridin-1(2H)-yl)-1-methyl-1H-benzimidazol-2-yl)cyclopropanecarboxylic acid (400 mg) and potassium carbonate (246 mg) in DMF (5 ml) at room temperature. The mixture was stirred at room temperature for 1 h. The mixture was quenched with water at room temperature and extracted with EtOAc. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by NH silica gel column chromatography (MeOH/EtOAc) to give the title compound (205 mg) as a pink solid.

Workup

  1. customThe mixture was quenched with water at room temperature
  2. extractionextracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by NH silica gel column chromatography (MeOH/EtOAc)

Sources & evidence

ORD record
ord-a7e488779859481fa57e8b0999f986bf
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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