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[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]

Synthesis of zomebazam

See also

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. ^ "Zomebazam". psychotropics.dk. 2003. Retrieved 7 December 2009.
  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. ^ 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