HCID 69720143, compound → HCID 22349310, compound

HRID 896391Notes

Reaction equation

HRID 896391 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][CH:26]=[C:27]([CH:28]=[CH:29][C:30]#[N:31])[C:16]=3[N:15]=2)[C:5]1=[O:32])([CH3:3])[CH3:2]>C1COCC1.CO.[Pd]>[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][CH:26]=[C:27]([CH2:28][CH2:29][C:30]#[N:31])[C:16]=3[N:15]=2)[C:5]1=[O:32])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 69720143HCID 69720143, compound

Product 1

HCID 22349310HCID 22349310, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[2-(3-isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-4-yl]-acrylonitrile (100 mg, 0.234 mmol) and 10% Pd-C (10 mg) in THF (2 mL) and methanol (25 mL) was rocked in a Parr shaker under a hydrogen atmosphere (50 psi) for 15 hrs. The catalyst was removed by filtration and the filtrate purified by flash chromatography (eluent hexane:ethyl acetate 1:1) to afford 3-[2-(3-Isopropyl-2-oxo-2,3-dihydro-benzoimidazol-1-ylmethyl)-1-(3-methyl-butyl)-1H-benzoimidazol-4-yl]-propionitrile (74 mg, 74%) as a white solid:

Workup

  1. customfor 15 hrs
  2. customThe catalyst was removed by filtration
  3. customthe filtrate purified by flash chromatography (eluent hexane:ethyl acetate 1:1)

Sources & evidence

ORD record
ord-1e0b206e75ef48468b08e3cf4c7f343a
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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