Thiophenol → HCID 69103592、化合物

HRID 2217263ノート

反応式

HRID 2217263 の反応式
[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

参加物

7

反応物 4

HCID 7969ThiophenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11429076HCID 11429076、化合物

生成物 1

HCID 69103592HCID 69103592、化合物収率 86.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d290300cc1514dcdacdeaf4dde59d11a
出典データセット
uspto-grants-2008_08
特許番号
US07407961B2

反応ノート

読み込み中…