Acrylamide → HCID 69102834, compound

HRID 2217253Notes

Reaction equation

HRID 2217253 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[N:6][C:7]=1Br.[C:25]([NH2:29])(=[O:28])[CH:26]=[CH2:27].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Pd+2].O.CCOC(C)=O.CN(C=O)C>[NH2:1][C:2]1[C:7](/[CH:27]=[CH:26]/[C:25]([NH2:29])=[O:28])=[N:6][C:5]([C:9]2[CH:10]=[CH:11][C:12](=[O:18])[N:13]([CH:15]([CH3:17])[CH3:16])[CH:14]=2)=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1

Participants

9

Reactant 4

HCID 6579AcrylamideHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 11429076HCID 11429076, compound

Product 1

HCID 69102834HCID 69102834, compoundYield 71.8%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg), acrylamide (55 mg), Pd(OAc)2 (3 mg), tris(2-methylphenyl)phosphine (8 mg), NEt3 (0.11 ml), and DMF (1.0 ml) was heated with stirring at 60° C. for 1 hour and then at 90° C. for 5 hours. After cooling, EtOAc and water were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was recrystallized from EtOAc and dried in vacuo to give (2E)-3-[3-amino-6-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridyl)-5-phenyl-2-pyrazinyl]acrylamide (70 mg).

Workup

  1. temperaturewas heated
  2. waitat 90° C. for 5 hours
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was recrystallized from EtOAc
  9. customdried in vacuo

Sources & evidence

ORD record
ord-7242127e39ac44d2977e96c9deb01698
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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