Dimethylformamide → 6-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

HRID 1876773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876773
Cl[C:2]1[CH:3]=C[C:5]([C:8]2[C:9]([C:17]([OH:19])=O)=[N:10][CH:11]=[C:12](C(=O)N)[N:13]=2)=[N:6][CH:7]=1.[CH3:20][N:21](C)C=O.S(Cl)(Cl)=[O:26].Cl[CH2:30][Cl:31]>>[Cl:31][C:30]1[CH:3]=[CH:2][C:7]([N:6]2[C:5](=[O:26])[C:8]3[C:9](=[N:10][CH:11]=[CH:12][N:13]=3)[C:17]2=[O:19])=[N:21][CH:20]=1

Komponenten

5

Edukt 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 68555708HCID 68555708, Verbindung

Produkt 1

HCID 64519736-(5-chloro-2-pyridyl)-5H-pyrrolo[3,4-b]pyrazine-5,7(6H)-dione

Reaktionsbedingungen

Temperatur
27.5 °C

Versuchsvorschrift

3-(5-Chloropyridin-2-yl)-carbamoylpyrazine-2-carboxylic acid (100 g) was suspended in 500 ml dichloromethane. The suspension was refluxed azeotropically for 60 min. The mixture was cooled to 25-30° C. and dimethyl formamide (2.6 gm) was added followed by addition of thionyl chloride (72 g) in 45-60 min at 25-30° C. The resulting mixture was refluxed till completion of reaction. The reaction mixture was concentrated to dryness at atmospheric pressure. Cooled the solid to 20-25° C. and 500 ml chilled water was added Cooled the slurry to 20-25° C. and stirred for 30 min. Slurry was filtered and washed with 200 ml water. The solid was dried at 60-70° C. to obtain 88 g of title compound.

Aufarbeitung

  1. temperatureThe suspension was refluxed azeotropically for 60 min
  2. temperatureThe resulting mixture was refluxed till completion of reaction
  3. concentrationThe reaction mixture was concentrated to dryness at atmospheric pressure
  4. temperatureCooled the solid to 20-25° C.
  5. temperature500 ml chilled water
  6. additionwas added
  7. temperatureCooled the slurry to 20-25° C.
  8. filtrationSlurry was filtered
  9. washwashed with 200 ml water
  10. customThe solid was dried at 60-70° C.

Quellen und Nachweise

ORD-Eintrag
ord-1c9ab743bcea4405bdf7d80cc1186b9e
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309723B2

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