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Dichloromethane → (S)-2-(9-neopentyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)ethyl acetate

HRID 132190
ノート
印刷プレビュー

反応式

HRID 132190 の反応式
O[CH2:2][C:3]1[C:11]([CH2:12][C@H:13]2[CH2:17][CH2:16][O:15][C:14]2=[O:18])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[N:6][NH:7]2.S(Cl)(Cl)=O.[C:23](=[O:26])([O-])[O-].[K+].[K+].[CH2:29]([NH2:34])[C:30]([CH3:33])([CH3:32])[CH3:31].Cl[CH2:36]Cl>>[C:14]([O:15][CH2:16][CH2:17][C@H:13]1[C:23](=[O:26])[N:34]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:2][C:3]2[C:4]3[CH:5]=[N:6][NH:7][C:8]=3[CH:9]=[CH:10][C:11]=2[CH2:12]1)(=[O:18])[CH3:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 79882NeopentylamineHCID 59731937(S)-3-((4-(hydroxymethyl)-1H-indazol-5-yl)methyl)-dihydrofuran-2(3H)-one

生成物 1

HCID 59731999(S)-2-(9-neopentyl-8-oxo-3,6,7,8,9,10-hexahydroazepino[3,4-e]indazol-7-yl)ethyl acetate
収率 19%

実験手順

(S)-3-((4-(hydroxymethyl)-1H-indazol-5-yl)methyl)-dihydrofuran-2(3H)-one (70 mg, 0.28 mmol), was dissolved in dichloromethane (1.5 mL). Thionyl chloride (500 μL) was added to the mixture. Reaction stirred at room temperature for 45 minutes. Mixture was concentrated. Residue was treated with dichloromethane and re-concentrated. Residue was dissolved in acetonitrile (3 mL). Potassium carbonate (150 mg, 1.1 mmol) was added to the mixture followed by neopentylamine (100 μL, 0.85 mmol). Mixture was heated at reflux for 45 minutes. Mixture was cooled to room temperature and filtered. Filtrate was concentrated in vacuo. Residue was dissolved in toluene (5 mL). Acetic acid (200 μL) was added to the mixture. Reaction was heated at reflux for 5.5 hours. Mixture was concentrated in vacuo. Preparatory HPLC purification gave the title compound as yellow solid in 19% yield.

後処理

  1. customReaction
  2. concentrationMixture was concentrated
  3. additionResidue was treated with dichloromethane
  4. concentrationre-concentrated
  5. dissolutionResidue was dissolved in acetonitrile (3 mL)
  6. temperatureMixture was heated
  7. temperatureat reflux for 45 minutes
  8. temperatureMixture was cooled to room temperature
  9. filtrationfiltered
  10. concentrationFiltrate was concentrated in vacuo
  11. dissolutionResidue was dissolved in toluene (5 mL)
  12. additionAcetic acid (200 μL) was added to the mixture
  13. customReaction
  14. temperaturewas heated
  15. temperatureat reflux for 5.5 hours
  16. concentrationMixture was concentrated in vacuo
  17. customPreparatory HPLC purification

出典と根拠

ORDレコード
ord-a7c3fbe428ca47989285011bec2611b5
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07384930B2

反応ノート

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