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Tetrahydrofuran → 1-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione

HRID 1677403
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1677403
[C:1]1([C:7](=[O:40])[CH2:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[N:11](S(C3C=CC(C)=CC=3)(=O)=O)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C[O:44]CC1.[OH-].[K+]>CO>[C:1]1([C:7](=[O:40])[C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:44])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 595410061-phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

Produkt 1

HCID 442060411-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

1-Phenyl-2-[5-(toluene-4-sulfonyl)-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone (100 mg, 0.18 mmol) was suspended in 4 ml of a 1:1 mixture of THF and methanol and 5N potassium hydroxide (0.180 ml, 0.9 mmol) was added dropwise. The reaction was heated at 40° C. for 2 hours. The solvents were evaporated using a rotary evaporator. Ethyl acetate and 1M hydrochloric acid were added to the residue and the layers were separated. The organic layer was washed with water, dried and concentrated. The crude reaction mixture was purified by preparative thin layer chromatography (50% ethyl acetate in hexanes) and flash chromatography to yield 4 mg of 1-phenyl-2-[2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethane-1,2-dione. MS: (M+H)+=418.

Aufarbeitung

  1. additionwas added dropwise
  2. customThe solvents were evaporated
  3. customa rotary evaporator
  4. additionEthyl acetate and 1M hydrochloric acid were added to the residue
  5. customthe layers were separated
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated
  9. customThe crude reaction mixture
  10. customwas purified by preparative thin layer chromatography (50% ethyl acetate in hexanes) and flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f1800cf426e4888ada5ae3946e40367
Quelldatensatz
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08008298B2

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