(2E)-N-[4-(diethylphosphonomethyl)phenyl]-3-[1-(4-fluorophenyl)-1H-imidazol-5-yl]acrylamide → HCID 86602525, compound

HRID 30711Notes

Reaction equation

HRID 30711 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:32])/[CH:18]=[CH:19]/[C:20]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:23]=[N:22][CH:21]=2)=[CH:12][CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]>[C].[Pd].C(O)C>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([NH:16][C:17](=[O:32])[CH2:18][CH2:19][C:20]2[N:24]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:23]=[N:22][CH:21]=2)=[CH:14][CH:15]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 86602526(2E)-N-[4-(diethylphosphonomethyl)phenyl]-3-[1-(4-fluorophenyl)-1H-imidazol-5-yl]acrylamide

Product 1

HCID 86602525HCID 86602525, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2E)-N-[4-(diethylphosphonomethyl)phenyl]-3-[1-(4-fluorophenyl)-1H-imidazol-5-yl]acrylamide (92 mg), 5% palladium-carbon (100 mg) and ethanol (10 ml) was stirred at room temperature under a hydrogen atmosphere at atmospheric pressure for 3 hrs. The reaction mixture was filtered, and the organic layer was concentrated to give N-[4-(diethylphosphonomethyl)phenyl]-3-[1-(4-fluorophenyl)-1H-imidazol-5-yl]propionamide (60 mg, 65%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-2fad04b4dc694123b46f898911b5f444
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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