Ethanol → Perampanel

HRID 2238571Notes

Reaction equation

HRID 2238571 reaction equation
O.[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11](=[O:28])[N:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:15]=1)#[N:3].C(O)C.Br.C(O)(=O)C>C(OCC)(=O)C>[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:11](=[O:28])[N:12]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:15]=1)#[N:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 68419241HCID 68419241, compound

Product 1

HCID 9924495PerampanelYield 112.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one hydrate (4.73 g, 3.25 mmol) and ethanol (small amount) was concentrated under reduced pressure, followed by adding ethyl acetate (small amount) to the residue before further concentration under reduced pressure. A 25% HBr/acetic acid solution (1.04 g, 4.2 mmol) was added to an ethyl acetate (30 mL) suspension containing the resultant residue, which was then stirred at room temperature for 3.5 hours. The precipitated solid was collected by filtration, washed with ethyl acetate (small amount), and then dried under reduced pressure to provide 1.28 g of the title compound as pale yellow crystals.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. additionby adding ethyl acetate (small amount) to the residue
  3. concentrationbefore further concentration under reduced pressure
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethyl acetate (small amount)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-eda53098eefb45378101a9005ba2721f
Source dataset
uspto-grants-2010_05
Patent number
US07718807B2

Reaction notes

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