HCID 178446108, compound → {3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester

HRID 896320Notes

Reaction equation

HRID 896320 reaction equation
[C:1]([O:5][C:6](=[O:37])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]3[CH:28]=[CH:29][C:30]([C:32](=[NH:35])[NH:33]O)=[CH:31][C:20]=3[N:19]=2)[C:9]1=[O:36])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.[Pd]>[C:1]([O:5][C:6](=[O:37])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]3[CH:28]=[CH:29][C:30]([C:32](=[NH:33])[NH2:35])=[CH:31][C:20]=3[N:19]=2)[C:9]1=[O:36])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 178446108HCID 178446108, compound

Product 1

HCID 20814118{3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl esterYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of {3-[5-(N-hydroxycarbamimidoyl)-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester (1.4 g, 2.76 mmol) in AcOH (50 ml) was added to 10% Pd/C (166 mg) and hydrogenated at 50 psi for 4 h then the mixture was filtered and washed with MeOH. The solvent was removed and the residue triturated with EtOAc to give 1 g (74%) of {3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester as a white solid.

Workup

  1. filtrationthe mixture was filtered
  2. washwashed with MeOH
  3. customThe solvent was removed
  4. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-709424ea241948698cb61d4ff6c7406a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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