HCID 66966480, compound → 3-(4-{6-[5-(4-Methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-propionic acid methyl ester

HRID 1513265Notes

Reaction equation

HRID 1513265 reaction equation
[CH3:1][O:2][C:3](=[O:36])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([C:27]5[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=5)=[N:25][N:26]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1>CCO.C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:36])[CH2:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[C:9]([C:13]2[NH:17][C:16]3[CH:18]=[C:19]([C:22]4[O:23][C:24]([C:27]5[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=5)=[N:25][N:26]=4)[CH:20]=[CH:21][C:15]=3[N:14]=2)=[C:8]([CH3:35])[CH:7]=1

Participants

4

Reactant 1

HCID 66966480HCID 66966480, compound

Product 1

HCID 669667773-(4-{6-[5-(4-Methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-propionic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of (E)-3-(4-{6-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-1H-benzoimidazol-2-yl}-3,5-dimethylphenyl)-acrylic acid methyl ester (1.0 g) in 40 mL EtOH/THF (1:1) was hydrogenated over 5% Pd/C (300 mg) at one atm for 3 h. The catalyst was filtered through Celite and was washed with EtOH and THF. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (heptane/EtOAc=1:2) to give the title compound. MS: m/z 483 (M+1).

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. washwas washed with EtOH and THF
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (heptane/EtOAc=1:2)

Sources & evidence

ORD record
ord-0be224b3022d42a889fd6a2f35ab5513
Source dataset
uspto-grants-2012_07
Patent number
US08217065B2

Reaction notes

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