HCID 58896535, compound → HCID 86612998, compound

HRID 2235537Notes

Reaction equation

HRID 2235537 reaction equation
[CH2:1]([N:8](CCC)[C:9]1[C:14]2[N:15]([CH3:28])[C:16]([NH:18][C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[N:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1C=CC=C[CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[C:20]1([CH3:27])[CH:21]=[C:22]([CH3:26])[CH:23]=[C:24]([CH3:25])[C:19]=1[NH:18][C:16]1[N:15]([CH3:28])[C:14]2[C:9]([NH:8][CH2:1][CH2:2][CH3:3])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Participants

4

Reactant 1

HCID 58896535HCID 58896535, compound

Product 1

HCID 86612998HCID 86612998, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 0.50 g (1.2 mmol) of N7-benzyl-N2-mesityl-1-methyl-N7-propyl-1H-benzimidazole-2,7-diamine in 30 mL of methanol was added 0.43 g (10 mol % Pd) of 20% Pearlman's catalyst (50% wet). The reaction was kept under a hydrogen atmosphere via a balloon and stirred at room temperature for 48 h. The catalyst was removed via filtration and the filtrate was concentrated in vacuo. Purification by flash chromatography eluting with a 7% methanol/dichloromethane mixture gave 0.23 g (58%) of the title compound as a cream colored solid.

Workup

  1. customThe catalyst was removed via filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customPurification by flash chromatography
  4. washeluting with a 7% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-ae21a99902dc49019d41d8b2bc59cbf4
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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