Zomebazam

Zomebazam
Identifiers
	IUPAC name 1,3,8-trimethyl-4-phenylpyrazolo[3,4-b][1,4]diazepine-5,7-dione;
CAS Number	78466-70-3 ;
PubChem CID	132677;
ChemSpider	117132 ;
UNII	G563Y6G60K;
CompTox Dashboard (EPA)	DTXSID60868481 ;
Chemical and physical data
Formula	C15H16N4O2
Molar mass	284.319 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1N(c2c(N(C(=O)C1)C)n(nc2C)C)c3ccccc3;
	InChI 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 ; Key:BFWACMHTIVUWJS-UHFFFAOYSA-N ;
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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

References

^ 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