Zomebazam[1] produced by Hoechst is a pyrazolodiazepinone derivative drug with anxiolytic properties. It is structurally related to razobazam and zometapine.[2]
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Formula | C15H16N4O2 |
Molar mass | 284.319 g·mol−1 |
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Synthesis
editThe catalytic hydrogenation of N,2,5-trimethyl-4-phenyldiazenylpyrazol-3-amine[a] (1) over Raney nickel gives 4-amino-1,3-dimethyl-5-methylaminopyrazole[b] (2). Treatment with methyl malonyl chloride[c] (3) gives 4-α-ethoxycarbonylacetylamino-1,3-dimethyl-5-methylaminopyrazole[d] (4). Base-catalyzed lactamization gives (5). The Goldberg reaction completes the synthesis of zomebazam (6).[3][4]
See also
editReferences
edit- ^ US 3558605, "4-Aryl-5,6,7,8-tetrahydropyrazolo(3,4-B)-(1,5)diazepine-1H,4H-5,7-diones and medicaments containing same"
- ^ "Zomebazam". psychotropics.dk. 2003. Retrieved 7 December 2009.
- ^ Renger B (1985). "Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion". Synthesis. 1985 (9): 856–560. doi:10.1055/s-1985-31364. S2CID 93397774.
- ^ US 4302468, Rackur G, Hoffmann I, issued 1981, assigned to Hoechst Aktiengesellschaft
Notes
edit- ^ CID:136203602
- ^ CID:10219477
- ^ CAS# [37517-81-0]
- ^ CID:20561101