HCID 178420401, compound → HCID 178516270, compound

HRID 493386Notes

Reaction equation

HRID 493386 reaction equation
C([O:8][C:9]1[CH:34]=[CH:33][C:12]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:21]=[C:22]([CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[NH:23][CH:24]=3)=[CH:16][CH:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)C.[Pd]>[O:26]([CH2:25][C:22]1[NH:23][CH:24]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([O:13][C:12]3[CH:11]=[CH:10][C:9]([OH:8])=[CH:34][CH:33]=3)=[CH:15][CH:16]=2)[N:21]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 1

HCID 178420401HCID 178420401, compound

Product 1

HCID 178516270HCID 178516270, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 100 ml reactor, 138 mg of 4-{4-[4-(benzyloxy)phenoxy]phenyl}-2-(phenoxymethyl)-1H-imidazole (0.0003 mol) in 10 ml of ethanol with a catalytic quantity of palladium adsorbed on carbon (10% by mass), are hydrogenated for 24 hours under a hydrogen pressure of 4 bars. The reaction medium is filtered on a millipore filter then rinsed with ethanol and evaporated to dryness. The residue is triturated with diethyl ether and the mixture is stirred in diethyl ether and the solid is filtered. The product obtained is adsorbed on silica then purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 2-8 to 5-5). After washing with diethyl ether, a white-coloured powder is obtained.

Workup

  1. filtrationThe reaction medium is filtered on a millipore
  2. filtrationfilter
  3. washthen rinsed with ethanol
  4. customevaporated to dryness
  5. customThe residue is triturated with diethyl ether
  6. filtrationthe solid is filtered
  7. customThe product obtained
  8. customthen purified by chromatography on a Biotage-type silica column (eluent: ethyl acetate-heptane: 2-8 to 5-5)
  9. washAfter washing with diethyl ether
  10. customa white-coloured powder is obtained

Sources & evidence

ORD record
ord-d0904bd446264ba3a919d56e87f2d553
Source dataset
uspto-grants-2009_05
Patent number
US07534805B2

Reaction notes

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