4-(benzyloxy)-1-(2-((1RS,2SR)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one → 4-Hydroxy-1-(2-((1RS,2SR)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

HRID 2203030Notes

Reaction equation

HRID 2203030 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:22]=[C:21]([CH:23]4[CH2:25][CH:24]4[C:26]([OH:29])([CH3:28])[CH3:27])[N:20]([CH3:30])[C:19]=3[CH:31]=2)[C:11](=[O:32])[CH:10]=1)C1C=CC=CC=1>[Pd].CO>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:22]=[C:21]([CH:23]4[CH2:25][CH:24]4[C:26]([OH:29])([CH3:27])[CH3:28])[N:20]([CH3:30])[C:19]=3[CH:31]=2)[C:11](=[O:32])[CH:10]=1

Participants

4

Reactant 1

HCID 897022104-(benzyloxy)-1-(2-((1RS,2SR)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one

Product 1

HCID 1213862594-Hydroxy-1-(2-((1RS,2SR)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-oneYield 89.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(benzyloxy)-1-(2-((1RS,2SR)-2-(2-hydroxypropan-2-yl)cyclopropyl)-1-methyl-1H-benzimidazol-6-yl)pyridin-2(1H)-one (1.35 g), 10% Pd/C (0.6 g) and MeOH (30 ml) was stirred under H2 atmosphere at room temperature for 3 h. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo to give the title compound (950 mg) as an off-white solid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-97a6b78399bd437d99cc4d3443523ea8
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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