HCID 22349403, compound → HCID 22349339, compound

HRID 896340Notes

Reaction equation

HRID 896340 reaction equation
C([O:8][CH2:9][C:10]1[N:14]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])[C:13]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:12]=2[N:11]=1)C1C=CC=CC=1>CO.Cl.[Pd]>[NH2:25][CH2:24][C:22]1[CH:21]=[CH:20][C:13]2[N:14]([CH2:15][CH2:16][CH:17]([CH3:18])[CH3:19])[C:10]([CH2:9][OH:8])=[N:11][C:12]=2[CH:23]=1

Participants

5

Reactant 1

HCID 22349403HCID 22349403, compound

Product 1

HCID 22349339HCID 22349339, compoundYield 137.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution 2-benzyloxymethyl-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (1.12 g, 3.36 mmol) in methanol (50 mL) and concentrated HCl (2.5 mL) was added 10% Pd/C (120 mg). This mixture was rocked under a hydrogen atmosphere in a Parr shaker(45 psi) for 48 hrs. The catalyst was removed by filtration and the solution concentrated in vacuo to give [5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-yl]-methanol (1.14 g, 100%) as a tan solid. A small portion was purified by prep HPLC (30-100% B) to give C-[2-Benzyloxymethyl-1-(3-methyl-butyl)-1H-benzoimidazol-5-yl]-methylamine; HCl salt:

Workup

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

Sources & evidence

ORD record
ord-9855211ff5ac4a848c3416db67c840fe
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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