Thionyl Chloride → HCID 19900415, compound

HRID 1199050Notes

Reaction equation

HRID 1199050 reaction equation
[Cl:1][CH:2]1[C:10]2[C:5](=CC=CC=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1.O[CH:24]1[C:32]2C(=NC=C[N:31]=2)C(=O)[N:25]1C1C=CC2C(=NC(OC)=CC=2)N=1.S(Cl)(Cl)=O>CN(C)C=O>[Cl:1][CH:2]1[C:10]2[C:5](=[N:25][CH:24]=[CH:32][N:31]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([Cl:22])=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 141824043-Chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinoneHCID 19900407HCID 19900407, compound

Product 1

HCID 19900415HCID 19900415, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-6-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazine is prepared in a manner similar to that described in Example 6 for the preparation of 3-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-1-isoindolinone, but starting with 5-hydroxy-6-(7-methoxy-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazine (23.2 g), sulphinyl chloride (300 cc) and dimethylformamide (1 cc). 5-Chloro-6-(7-chloro-1,8-naphthyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4-b]-pyrazine (21 g ) m.p. 264° C., is thereby obtained.

Workup

  1. custom5-Chloro-6-(7-chloro-1,8-naphthyridin-2-yl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazine is prepared in a manner similar to

Sources & evidence

ORD record
ord-7452febf78724a7aa3dfde9a9075a720
Source dataset
uspto-grants-1990_02
Patent number
US04898871

Reaction notes

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