Thiophenol → HCID 69103592, compound

HRID 2217263Notes

Reaction equation

HRID 2217263 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH2:10][C:11]1[N:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]([C:18]2[CH:19]=[CH:20][C:21](=[O:27])[N:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=2)=[N:15][C:16]=1Br.CCOC(C)=O>CN1C(=O)CCC1.O>[NH2:10][C:11]1[N:12]=[C:13]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:14]([C:18]2[CH:19]=[CH:20][C:21](=[O:27])[N:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=2)=[N:15][C:16]=1[S:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11429076HCID 11429076, compound

Product 1

HCID 69103592HCID 69103592, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% NaH (52 mg) in NMP (1.0 ml), was added thiophenol (143 mg) under ice-bath cooling. After 10 minute stirring, 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg) was added to the mixture at the same temperature. The mixture was stirred at the same temperature for 10 minutes and then allowed to warm to 25° C. After 2 hours stirring, the mixture was heated at 100° C. for 1 hour. 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 MeOH-IPE to give 5-[5-amino-3-phenyl-6-(phenylthio)-2-pyrazinyl]-1-isopropyl-2(1H)-pyridone (93 mg).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 10 minutes
  3. stirringAfter 2 hours stirring
  4. temperaturethe mixture was heated at 100° C. for 1 hour
  5. temperatureAfter cooling
  6. customthe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. customThe solvent was removed under reduced pressure
  10. customThe residue was recrystallized from MeOH-IPE

Sources & evidence

ORD record
ord-d290300cc1514dcdacdeaf4dde59d11a
Source dataset
uspto-grants-2008_08
Patent number
US07407961B2

Reaction notes

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