Zomebazam

Zomebazam
Identifiers
  • 1,3,8-trimethyl-4-phenylpyrazolo[3,4-b][1,4]diazepine-5,7-dione
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H16N4O2
Molar mass284.319 g·mol−1
3D model (JSmol)
  • O=C1N(c2c(N(C(=O)C1)C)n(nc2C)C)c3ccccc3
  • InChI=1S/C15H16N4O2/c1-10-14-15(18(3)16-10)17(2)12(20)9-13(21)19(14)11-7-5-4-6-8-11/h4-8H,9H2,1-3H3 ☒N
  • Key:BFWACMHTIVUWJS-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

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

Synthesis

[edit]

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

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References

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  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

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