반응 #94627

반응 방정식

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

수율 41.2%

용매

acetonitrile

ethanol

반응 조건

후처리

1. 1
   온도the reaction mixture is heated at the reflux temperature for 13 hours
2. 2
   온도After cooling
3. 3
   여과the insoluble product is filtered off
4. 4
   세척washed 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
   기타the solution obtained
7. 7
   기타The organic layer is decanted
8. 8
   세척washed with water (2 × 50 cc.)
9. 9
   건조dried over anhydrous sodium sulphate in the presence of decolourising charcoal
10. 10
    여과filtered
11. 11
    기타evaporated to dryness under reduced pressure
12. 12
    기타The residue is recrystallised from acetonitrile (95 cc.)
13. 13
    기타the product obtained
14. 14
    기타The insoluble product is then isolated from the boiling solution by filtration
15. 15
    세척after which it is washed with boiling ethanol (2 × 10 cc.)
16. 16
    기타After drying

실험 절차

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.

출처