Thiophenol → HCID 69103592, 화합물

HRID 2217263노트

반응식

HRID 2217263 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 69103592HCID 69103592, 화합물수율 86.4%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
25 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d290300cc1514dcdacdeaf4dde59d11a
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407961B2

반응 노트

불러오는 중…