7-(Benzyloxy)-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide → 7-Hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

HRID 1258464Notes

Reaction equation

HRID 1258464 reaction equation
C([O:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:10]=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[C:14]2[N:15]([CH2:19][CH2:20][O:21][CH3:22])[C:16]([CH3:18])=[N:17][C:13]=2[CH:12]=[C:11]([C:23]([N:25]([CH3:27])[CH3:26])=[O:24])[CH:10]=1

Participants

4

Reactant 1

HCID 672195137-(Benzyloxy)-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide

Product 1

HCID 672205657-Hydroxy-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamideYield 95.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-(benzyloxy)-1-(2-methoxyethyl)-N,N,2-trimethyl-1H-benzimidazole-5-carboxamide (483 mg, 1.31 mmol, Step 1) and 10% palladium-carbon (50 mg) in ethanol (30 mL) was stirred under hydrogen gas for 19 hours. The resulting mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuo to afford the title compound as a white solid (347 mg, 95%).

Workup

  1. filtrationThe resulting mixture was filtered through a pad of Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-cd9460dcdc2e4ec09633ff2edc89949b
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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