HCID 86630625, compound → HCID 68615718, compound

HRID 643714Notes

Reaction equation

HRID 643714 reaction equation
[N:1]([CH2:4][C:5]([S:8]([C:11]1[CH:28]=[CH:27][C:14]2[N:15]([CH2:23][CH:24]3[CH2:26][CH2:25]3)[C:16]([CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:17][C:13]=2[CH:12]=1)(=[O:10])=[O:9])([CH3:7])[CH3:6])=[N+]=[N-]>[C].[Pd].CO>[CH:24]1([CH2:23][N:15]2[C:14]3[CH:27]=[CH:28][C:11]([S:8]([C:5]([CH3:6])([CH3:7])[CH2:4][NH2:1])(=[O:10])=[O:9])=[CH:12][C:13]=3[N:17]=[C:16]2[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 86630625HCID 86630625, compound

Product 1

HCID 68615718HCID 68615718, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-[(2-azido-1,1-dimethylethyl)sulfonyl]-1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazole (Step J, 265 mg, 0.66 mmol), 10% palladium carbon (30 mg) and methanol (8 mL) was stirred at room temperature for 18 h under hydrogen atmosphere. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1 as eluent) to afford the title compound (199 mg, 80%) as a white brown solid.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=15:1 as eluent)

Sources & evidence

ORD record
ord-7dc9dbbd4970490ea041e231a93be688
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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