Zomebazam

Zomebazam

Zomebazam

Chemical compound

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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Synthesis

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

Synthesis of zomebazam

See also

References

  1. [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. [2]
    "Zomebazam". psychotropics.dk. 2003. Retrieved 7 December 2009.
  3. [3]
    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.
  4. [4]
    US 4302468, Rackur G, Hoffmann I, issued 1981, assigned to Hoechst Aktiengesellschaft

Notes

  1. CID:136203602
  2. CID:10219477
  3. CAS# [37517-81-0]
  4. CID:20561101
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