Methanol → HCID 121386234, compound

HRID 2202874Notes

Reaction equation

HRID 2202874 reaction equation
[BH4-].[Na+].[CH:3]1([C:6]([C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[C:15]([N:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)=[CH:20][C:19]4=[O:33])[CH:16]=[CH:17][C:10]=3[N:9]=2)=[O:7])[CH2:5][CH2:4]1.CO>C1COCC1>[CH:3]1([CH:6]([OH:7])[C:8]2[N:12]([CH3:13])[C:11]3[CH:14]=[C:15]([N:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)=[CH:20][C:19]4=[O:33])[CH:16]=[CH:17][C:10]=3[N:9]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 89691290HCID 89691290, compound

Product 1

HCID 121386234HCID 121386234, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (10.9 mg) was added to a solution of 1-(2-(cyclopropylcarbonyl)-1-methyl-1H-benzimidazol-6-yl)-4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (60.0 mg) in THF (2 ml)-MeOH (0.2 ml) at room temperature. The mixture was stirred at room temperature for 30 min. The mixture was quenched with water and extracted with EtOAc/THF twice. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The solid was washed with Et2O to give the title compound (47.9 mg) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-8374ddc5544a4491beb32392b512fe85
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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