1-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one → 1-[5-amino-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

HRID 896332Notes

Reaction equation

HRID 896332 reaction equation
C(=[N:14][C:15]1[CH:42]=[CH:41][C:18]2[N:19]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:20]([CH2:22][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]([CH:32]([CH3:34])[CH3:33])[C:24]3=[O:35])=[N:21][C:17]=2[CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1>Cl.C1COCC1>[NH2:14][C:15]1[CH:42]=[CH:41][C:18]2[N:19]([CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])[C:20]([CH2:22][N:23]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[N:25]([CH:32]([CH3:34])[CH3:33])[C:24]3=[O:35])=[N:21][C:17]=2[CH:16]=1

Participants

3

Reactant 1

HCID 865901151-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one

Product 1

HCID 208139871-[5-amino-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-oneYield 85.1%

Reagents, catalysts & solvents 1

HCID 18422008HCl tetrahydrofuranSolvent

Procedure

A solution of 1-[5-(benzhydrylidene-amino)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one (32 mg, 0.06 mmol) in 0.5 M HCl-THF was stirred at ambient temperature for 1 h. The solvent was evaporated and the residue purified by prep-HPLC (gradient 10%-100% B) to give 20 mg (85%) of 1-[5-amino-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-3-isopropyl-1,3-dihydro-benzoimidazol-2-one as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by prep-HPLC (gradient 10%-100% B)

Sources & evidence

ORD record
ord-e439695ebeba47b198adeab96bb92e31
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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