1-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid → 1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carboxylic acid

HRID 1750206Notes

Reaction equation

HRID 1750206 reaction equation
[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:18][C:19]1[O:20][CH:21]=[CH:22][CH:23]=1)[CH2:4][CH3:5])[CH3:2]>C(O)C.[Pt]=O>[CH2:1]([CH:3]([N:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]([OH:17])=[O:16])=[CH:14][C:9]=2[N:8]=[C:7]1[CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 1

HCID 867144171-(1-Ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid

Product 1

HCID 867143751-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carboxylic acidYield 17%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A solution of 348 mg of 1-(1-ethyl-propyl)-2-furan-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid in 5 ml of ethanol was hydrogenated at 5 bar for 24 h in the presence of 10 mg platinum oxide. The catalyst was removed by filtration, and the filtrate was concentrated in vacuo. The resulting residue was purified by HPLC to obtain 55 mg (17%) of 1-(1-Ethyl-propyl)-2-(tetrahydro-furan-2-ylmethyl)-1H-benzoimidazole-5-carboxylic acid.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by HPLC

Sources & evidence

ORD record
ord-0810db3c636c4a0a95930f0de9041e61
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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