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

HRID 328278Notes

Reaction equation

HRID 328278 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[C:19]4[C:14](=[N:15][CH:16]=[CH:17][N:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:4][N:3]=1.ClC(OC1C=CC=CC=1)=O.ClC1N=C2C(C=CC(N3C(O)C4C(=NC=CN=4)C3=O)=N2)=CC=1>N1C=CC=CC=1>[Cl:1][C:2]1[N:3]=[C:4]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[C:19]4[C:14](=[N:15][CH:16]=[CH:17][N:18]=4)[C:13]3=[O:31])=[N:9]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 64531286-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-oneHCID 21444365HCID 21444365, compound

Product 1

HCID 233436456-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

6-(7-Chloro-1,6-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine can be prepared by adding phenyl chloroformate (9.4 g.) 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 (6.3 g.) in anhydrous pyridine (63 cc.), with stirring and whilst keeping the temperature at about 5° C. When the addition is complete, the reaction mixture is gradually heated to 60° C. and this temperature is maintained for 1 hour. The reaction mixture is cooled and is then poured into distilled water (350 cc.) whilst keeping the temperature at about 10° C. The insoluble product is filtered off, and washed successively with water (120 cc.), acetonitrile (40 cc.) and diisopropyl ether (40 cc.). After drying, 6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-5-phenoxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (7.2 g.), melting at 270° C., is obtained.

Workup

  1. customat about 5° C
  2. additionWhen the addition
  3. temperaturethis temperature is maintained for 1 hour
  4. temperatureThe reaction mixture is cooled
  5. additionis then poured
  6. distillationinto distilled water (350 cc.)
  7. customat about 10° C
  8. filtrationThe insoluble product is filtered off
  9. washwashed successively with water (120 cc.), acetonitrile (40 cc.) and diisopropyl ether (40 cc.)
  10. customAfter drying

Sources & evidence

ORD record
ord-5d93775bb2da456e9b43607f723e0e81
Source dataset
uspto-grants-1977_04
Patent number
US04016274

Reaction notes

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