StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dichloromethane → 6-(7-Chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrole(3,4-b)pyrazin-5-yl dimethylcarbamate

HRID 2083740
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2083740
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[O:4].C(N(CC)CC)C.[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([OH:34])[C:32]4[C:27](=[N:28][CH:29]=[CH:30][N:31]=4)[C:26]3=[O:35])=[N:22]2)=[CH:17][CH:16]=1.C(Cl)Cl>C(#N)C.CN(C)C=O.O.N1C=CC=CC=1>[Cl:14][C:15]1[N:24]=[C:23]2[C:18]([CH:19]=[CH:20][C:21]([N:25]3[CH:33]([O:34][C:3]([N:2]([CH3:6])[CH3:1])=[O:4])[C:32]4[C:27](=[N:28][CH:29]=[CH:30][N:31]=4)[C:26]3=[O:35])=[N:22]2)=[CH:17][CH:16]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 6344DichloromethaneHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 64531286-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

Produkt 1

HCID 227547576-(7-Chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrole(3,4-b)pyrazin-5-yl dimethylcarbamateAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittel2×HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethylcarbamoyl chloride (4.85 g.) and triethylamine (4.55 g.) are added successively to a suspension of 6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (4.7 g.) in a mixture of anhydrous methylene chloride (47 cc.) and anhydrous pyridine (16 cc.). The reaction mixture is heated at the reflux temperature for 2 hours, and is then cooled and poured into water (180 cc.). A slight amount of insoluble matter is filtered off and the aqueous layer is decanted off and washed with methylene chloride (2 × 50 cc.) by successive decantations. The combined organic layers are washed by successive decantations with 1N sodium hydroxide solution (2 × 30 cc.) and water (2 × 30 cc.), dried with anhydrous sodium sulphate in the presence of decolourising charcoal, filtered and evaporated to dryness under reduced pressure. The residue obtained is taken up in acetonitrile (20 cc.) and the insoluble product is filtered off and washed with acetonitrile (3 × 2 cc.). Recrystallisation of this product from dimethylformamide (14 cc.) gives a solvated product (4.1 g.). This product is dissolved in dimethylformamide (100 cc.) at a temperature of about 70° C. The solution thus obtained is poured into water (1,200 cc.) and the insoluble product is filtered off and washed with water (5 × 20 cc.). After drying, 6-(7-chloro-1,8-naphthyridin-2-yl)-5-dimethylaminocarbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (3.6 g.), melting at 270° C., is obtained.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at the reflux temperature for 2 hours
  2. temperatureis then cooled
  3. filtrationA slight amount of insoluble matter is filtered off
  4. customthe aqueous layer is decanted off
  5. washwashed with methylene chloride (2 × 50 cc.) by successive decantations
  6. washThe combined organic layers are washed by successive decantations with 1N sodium hydroxide solution (2 × 30 cc.) and water (2 × 30 cc.)
  7. dry with materialdried with anhydrous sodium sulphate in the presence of decolourising charcoal
  8. filtrationfiltered
  9. customevaporated to dryness under reduced pressure
  10. customThe residue obtained
  11. filtrationthe insoluble product is filtered off
  12. washwashed with acetonitrile (3 × 2 cc.)
  13. customRecrystallisation of this product from dimethylformamide (14 cc.)
  14. customgives a solvated product (4.1 g.)
  15. customThe solution thus obtained
  16. filtrationthe insoluble product is filtered off
  17. washwashed with water (5 × 20 cc.)
  18. customAfter drying

Quellen und Nachweise

ORD-Eintrag
ord-96d146e9ed1047ee8f2368776619931d
Quelldatensatz
uspto-grants-1978_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04086348

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion