Reaktion #94627

Reaktionsgleichung

sodium hydroxide

Cyclohexyl isocyanate

6-(7-chloro-1,8-naphthyridin-2-yl)-5-hydroxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

triethylamine

→

6-(7-chloro-1,8-naphthyridin-2-yl)-5-cyclohexylaminocarbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

Ausbeute 41.2%

Lösungsmittel

acetonitrile

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture is heated at the reflux temperature for 13 hours
2. 2
   TemperaturAfter cooling
3. 3
   Filtrationthe insoluble product is filtered off
4. 4
   Waschenwashed successively with acetonitrile (2 × 10 cc.) and diisopropyl ether (2 × 20 cc.)
5. 5
   workup.DISSOLUTIONIt is then dissolved in methylene chloride (300 cc.)
6. 6
   Sonstigethe solution obtained
7. 7
   SonstigeThe organic layer is decanted
8. 8
   Waschenwashed with water (2 × 50 cc.)
9. 9
   Trocknendried over anhydrous sodium sulphate in the presence of decolourising charcoal
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated to dryness under reduced pressure
12. 12
    SonstigeThe residue is recrystallised from acetonitrile (95 cc.)
13. 13
    Sonstigethe product obtained
14. 14
    SonstigeThe insoluble product is then isolated from the boiling solution by filtration
15. 15
    Waschenafter which it is washed with boiling ethanol (2 × 10 cc.)
16. 16
    SonstigeAfter drying

Vorschrift

Cyclohexyl isocyanate (1.38 g.) is added 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 (3.12 g.) in anhydrous acetonitrile (60 cc.) in the presence of triethylamine (1 cc.), and the reaction mixture is heated at the reflux temperature for 13 hours. After cooling, the insoluble product is filtered off and washed successively with acetonitrile (2 × 10 cc.) and diisopropyl ether (2 × 20 cc.). It is then dissolved in methylene chloride (300 cc.) and the solution obtained is stirred for 15 minutes with 1N sodium hydroxide solution (50 cc.). The organic layer is decanted, washed with water (2 × 50 cc.), dried over anhydrous sodium sulphate in the presence of decolourising charcoal, filtered and then evaporated to dryness under reduced pressure. The residue is recrystallised from acetonitrile (95 cc.) and the product obtained is heated for 10 minutes with ethanol (65 cc.) at the reflux temperature. The insoluble product is then isolated from the boiling solution by filtration, after which it is washed with boiling ethanol (2 × 10 cc.). After drying, 6-(7-chloro-1,8-naphthyridin-2-yl)-5-cyclohexylaminocarbonyloxy-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (1.8 g.), melting at 264° C., is obtained.

Quelle