3-[4-(benzyloxy)phenyl]-1-ethyl-7-(trifluoromethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one → HCID 58577261, compound

HRID 1430040Notes

Reaction equation

HRID 1430040 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][C:23]([C:24]([F:27])([F:26])[F:25])=[C:18]3[N:17]([CH2:28][CH3:29])[C:16]2=[O:30])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].CO.CCOC(C)=O>[CH2:28]([N:17]1[C:18]2[C:19](=[N:20][CH:21]=[CH:22][C:23]=2[C:24]([F:26])([F:25])[F:27])[N:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)[C:16]1=[O:30])[CH3:29]

Participants

5

Reactant 1

HCID 585777233-[4-(benzyloxy)phenyl]-1-ethyl-7-(trifluoromethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Product 1

HCID 58577261HCID 58577261, compoundYield 66.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-[4-(benzyloxy)phenyl]-1-ethyl-7-(trifluoromethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (197 mg) and 10% palladium on carbon (50% wet, 68 mg) in MeOH (6.5 mL) and EtOAc (6.5 mL) was hydrogenated under balloon pressure at room temperature for 4 h. The solid was filtrated and washed with MeOH (10 mL) to remove the catalyst. The filtrate was concentrated in vacuo to give the title compound (103 mg).

Workup

  1. filtrationThe solid was filtrated
  2. washwashed with MeOH (10 mL)
  3. customto remove the catalyst
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ae955807137344bca755159def7689f3
Source dataset
uspto-grants-2015_01
Patent number
US08940758B2

Reaction notes

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