Dimethylformamide → HCID 121386237, compound

HRID 2202875Notes

Reaction equation

HRID 2202875 reaction equation
[H-].[Na+].[CH:3]1([CH:6]([OH:33])[C:7]2[N:11]([CH3:12])[C:10]3[CH:13]=[C:14]([N:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[CH:19][C:18]4=[O:32])[CH:15]=[CH:16][C:9]=3[N:8]=2)[CH2:5][CH2:4]1.IC.[CH3:36]N(C=O)C>C1COCC1>[CH:3]1([CH:6]([O:33][CH3:36])[C:7]2[N:11]([CH3:12])[C:10]3[CH:13]=[C:14]([N:17]4[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]5[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=5)=[CH:19][C:18]4=[O:32])[CH:15]=[CH:16][C:9]=3[N:8]=2)[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 121386234HCID 121386234, compound

Product 1

HCID 121386237HCID 121386237, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (40% oil dispersion, 5.2 mg) was added to a solution of 1-(2-(cyclopropyl(hydroxy)methyl)-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (30 mg) and iodomethane (0.013 ml) in THF (2 ml)-DMF (1 ml) at room temperature. The mixture was stirred at room temperature for 30 min. The mixture was quenched with water and extracted with EtOAc twice. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting solid was washed with Et2O to give the title compound (23.6 mg) as a white solid.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc twice
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. washThe resulting solid was washed with Et2O

Sources & evidence

ORD record
ord-58096b121c4e4f09bbe73b468f718dc2
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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