Zomebazam Explained

Zomebazam^[1] produced by Hoechst is a pyrazolodiazepinone derivative drug with anxiolytic properties. It is structurally related to razobazam and zometapine.^[2]

Synthesis

The catalytic hydrogenation of N,2,5-trimethyl-4-phenyldiazenylpyrazol-3-amine (1) over Raney nickel gives 4-amino-1,3-dimethyl-5-methylaminopyrazole (2). Treatment with methyl malonyl chloride (3) gives 4-α-ethoxycarbonylacetylamino-1,3-dimethyl-5-methylaminopyrazole (4). Base-catalyzed lactamization gives (5). The Goldberg reaction completes the synthesis of zomebazam (6).^{[3] [4]}

See also

• Benzodiazepine

Notes and References

1. US . 3558605 . 4-Aryl-5,6,7,8-tetrahydropyrazolo(3,4-B)-(1,5)diazepine-1H,4H-5,7-diones and medicaments containing same .
2. Web site: Zomebazam . 7 December 2009 . 2003 . psychotropics.dk .
3. Renger B . Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion. . Synthesis . 1985 . 1985 . 9 . 856–560 . 10.1055/s-1985-31364. 93397774 .
4. US . 4302468 . Rackur G, Hoffmann I . 1981 . Hoechst Aktiengesellschaft .