4-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide → 4-Hydroxy-N,N,2-trimethyl-1-((4-methylphenyl)sulfonyl)-1H-benzimidazole-6-carboxamide

HRID 2239298Notes

Reaction equation

HRID 2239298 reaction equation
[CH3:1][N:2]([CH3:33])[C:3]([C:5]1[CH:6]=[C:7]([O:25]CC2C=CC=CC=2)[C:8]2[N:12]=[C:11]([CH3:13])[N:10]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[C:9]=2[CH:24]=1)=[O:4]>[Pd].O1CCCC1>[OH:25][C:7]1[C:8]2[N:12]=[C:11]([CH3:13])[N:10]([S:14]([C:17]3[CH:18]=[CH:19][C:20]([CH3:23])=[CH:21][CH:22]=3)(=[O:16])=[O:15])[C:9]=2[CH:24]=[C:5]([C:3]([N:2]([CH3:33])[CH3:1])=[O:4])[CH:6]=1

Participants

4

Reactant 1

HCID 672201744-(Benzyloxy)-N,N,2-trimethyl-1-tosyl-1H-benzo[d]imidazole-6-carboxamide

Product 1

HCID 672203154-Hydroxy-N,N,2-trimethyl-1-((4-methylphenyl)sulfonyl)-1H-benzimidazole-6-carboxamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N,N,2-trimethyl-1-[(4-methylphenyl)sulfonyl]-4-[(phenylmethyl)oxy]-1H-benzimidazole-6-carboxamide (29.0 g, 62.6 mmol, STEP 3) and 10% palladium on carbon (6.0 g) in tetrahydrofuran (200 mL) was stirred under hydrogen gas (1 atmosphere) at room temperature for 24 hours. Another 4.0 g of 10% palladium on carbon was added, and the mixture was stirred under hydrogen gas (1 atmosphere) at room temperature for additional 6 hours. The resulted mixture was filtered through a pad of Celite, and the filtrate was concentrated in vacuum to afford the title compound as a white solid (23.0 g, 98%).

Workup

  1. stirringthe mixture was stirred under hydrogen gas (1 atmosphere) at room temperature for additional 6 hours
  2. filtrationThe resulted mixture was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated in vacuum

Sources & evidence

ORD record
ord-d69604e5e2d9426d8520556b45fe5af9
Source dataset
uspto-grants-2010_05
Patent number
US07723321B2

Reaction notes

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