反応 #94627

反応方程式

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

収率 41.2%

溶媒

acetonitrile

ethanol

反応条件

後処理

1. 1
   温度the reaction mixture is heated at the reflux temperature for 13 hours
2. 2
   温度After cooling
3. 3
   ろ過the insoluble product is filtered off
4. 4
   洗浄washed 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
   その他the solution obtained
7. 7
   その他The organic layer is decanted
8. 8
   洗浄washed with water (2 × 50 cc.)
9. 9
   乾燥dried over anhydrous sodium sulphate in the presence of decolourising charcoal
10. 10
    ろ過filtered
11. 11
    その他evaporated to dryness under reduced pressure
12. 12
    その他The residue is recrystallised from acetonitrile (95 cc.)
13. 13
    その他the product obtained
14. 14
    その他The insoluble product is then isolated from the boiling solution by filtration
15. 15
    洗浄after which it is washed with boiling ethanol (2 × 10 cc.)
16. 16
    その他After drying

実験手順

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.

出典