2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile → 1-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

HRID 896300Notes

Reaction equation

HRID 896300 reaction equation
[CH:1]([N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:17]3[CH:24]=[CH:25][C:26]([C:28]#[N:29])=[CH:27][C:16]=3[N:15]=2)[C:5]1=[O:30])([CH3:3])[CH3:2]>[Pd].Cl.CO>[NH2:29][CH2:28][C:26]1[CH:25]=[CH:24][C:17]2[N:18]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:14]([CH2:13][N:6]3[C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[N:4]([CH:1]([CH3:2])[CH3:3])[C:5]3=[O:30])=[N:15][C:16]=2[CH:27]=1

Participants

4

Reactant 1

HCID 223493242-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile

Product 1

HCID 116758201-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-oneYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21893726Hydrochloride methanolSolvent

Procedure

A mixture of 2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazole-5-carbonitrile (230 mg, 0.57 mmol) and 10% palladium on carbon (50 mg) in 5% HCl-MeOH (10 mL) was placed in a Parr shaker under hydrogen (40 psi) for 6 h. The reaction mixture was filtered through celite and the solvent evaporated. The residue was purified by prep-HPLC (gradient 10% -100% B) to give 148 mg (64%) of 1-[5-aminomethyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a hygroscopic white solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe solvent evaporated
  3. customThe residue was purified by prep-HPLC (gradient 10% -100% B)

Sources & evidence

ORD record
ord-495703a3ae424f09af52c2175ff217b8
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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