Zopiclone → 3-(5-Chloropyrid-2-yl)carbamoylpyrazine-2-carboxylic acid

HRID 507798

Reaktionsgleichung

Reaktionsgleichung von HRID 507798
CN1CCN(C([O:10][CH:11]2[N:20]([C:21]3[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][N:26]=3)[C:18](=[O:19])[C:13]3[N:14]=[CH:15][CH:16]=[N:17][C:12]2=3)=O)CC1.NC1C=CC(Cl)=CN=1.N1C=CN=C2C(OC(=O)C=12)=[O:43]>>[Cl:27][C:24]1[CH:23]=[CH:22][C:21]([NH:20][C:18]([C:13]2[C:12]([C:11]([OH:43])=[O:10])=[N:17][CH:16]=[CH:15][N:14]=2)=[O:19])=[N:26][CH:25]=1

Komponenten

4

Edukt 3

HCID 5735ZopicloneHCID 661742-Amino-5-chloropyridineHCID 78482Furo(3,4-b)pyrazine-5,7-dione

Produkt 1

HCID 32808183-(5-Chloropyrid-2-yl)carbamoylpyrazine-2-carboxylic acid

Versuchsvorschrift

U.S. Pat. No. 3,862,149 describes a process for preparing zopiclone. The process comprises reacting 2-amino-5-chloropyridine with pyrazine 2,3-dicarboxylic acid anhydride to obtain 3-(5-chloropyrid-2-yl)carbamoyl-pyrazine-2-carboxylic acid, which is further treated with thionyl chloride to obtain 6-(5-chloropyrid-2-yl)-5,7-dioxo-5,6-dihydro-5H-pyrrolo[3,4-b]pyrazine 6-(5-chloropyrid-2-yl)-5,7-dioxo-5,6-dihydro-5H-pyrrolo[3,4-b]pyrazine is reduced using potassium borohydride in a mixture of dioxane and water followed by neutralization with acetic acid to obtain 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydro-5H-pyrrolo[3,4-b]-pyra-zine. The reaction of 6-(5-chloropyrid-2-yl)-5-hydroxy-7-oxo-5,6-dihydro-5H-pyrrolo[3,4-b]pyra-zine with 1-chlorocarbonyl-4-methyl piperazine in anhydrous dimethyl formamide and sodium hydride (50% dispersion in mineral oil) yields the final product, Zopiclone.

Quellen und Nachweise

ORD-Eintrag
ord-f814e4fd4a4546af952b97b001be3fdc
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786304B2

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