78466-70-3 Usage
Originator
Zomebazam,ZYF Pharm Chemical
Manufacturing Process
(a) 1,3,8-Trimethyl-4-phenyl-5,6,7,8-tetrahydropyrazolo[3,4-b][1,5]diazepine-
1H ,4H-5,7-dione:
23 g (0.1 mole) of 4-benzene-azo-1,3-dimethyl-5-methylaminopyrazole are
hydrogenated in 250 ml of ethanol with 60 g of Raney nickel, at 60°C; a
hydrogen pressure of 50 atmospheres. When the uptake of hydrogen has
ended, the catalyst is filtered off and the reaction solution is evaporated in
vacuum. The residue is triturated with ether/petroleum ether and the
precipitate of 4-amino-1,3-dimethyl-5-methylaminopyrazole is filtered off. The
product is sufficiently pure for the subsequent reactions. MP: 87°C.
(b) 4-α-Ethoxycarbonylacetylamino-1,3-dimethyl-5-methylaminopyrazole:
1.4 g (0.01 mole) of 4-amino-1,3-dimethyl-5-methylaminopyrazole are
dissolved in 20 ml of toluene, 1 ml (0.012 mole) of monomethyl malonate
chloride is slowly added dropwise, whilst cooling with ice, and the mixture is
subsequently stirred at room temperature for one hour. The toluene is
stripped off in vacuum, the residue is taken up in chloroform and the mixture
is washed with ice-cold NaHCO 3 solution and water and dried with Na 2 SO 4 .
After evaporating off the solvent, 4-α-ethoxycarbonylacetylamino-1,3-
dimethyl-5-methylaminopyrazole remains as an yellowish oil.
(c) 1,3,8-Trimethyl-5,6,7,8-tetrahydropyrazolo[3,4-b][1,5]diazepine-1H,4H-5,7-dione:
15 ml of a 1 molar sodium methanolate solution are added to 2.4 g (0.01
mole) of 4-α-ethoxycarbonylacetylamino-1,3-dimethyl-5-methyl-
aminopyrazole, dissolved in 100 ml of ethanol, and the mixture is stirred at
room temperature for 8 hours. It is then neutralized with alcoholic HCl and
evaporated in vacuum, the residue is taken up in CHCl 3 , the mixture is filtered
and the filtrate is again evaporated. After adding ether to the residue, the
latter becomes crystalline and can be filtered off. It is recrystallized from
isopropanol/diisopropyl ether. MP: 202°C.
(d) 1,3,8-Trimethyl-4-phenyl-5,6,7,8-tetrahydropyrazolo[3,4-b][1,5]diazepine-
1H,4H-5,7-dione:
A mixture of 1 g of 1,3,8-trimethyl-5,6,7,8-tetrahydropyrazolo[3,4-
b][1,5]diazepine-1H,4H-5,7-dione, 1 g of potassium acetate and 1.5 g of
copper powder in 100 ml of bromobenzene is boiled under reflux, whilst
stirring, until the reaction has ended (monitoring by thin layer
chromatography, 3-4 hours). The mixture is then allowed to cool to room
temperature and is diluted with CH 2 Cl 2 (200 ml), the inorganic constituents
are filtered off, the organic phase is washed with water and dried and the
solvent is stripped off in vacuum. Recrystallization of the residue from
diisopropyl ether gives the analytically pure 1,3,8-trimethyl-4-phenyl-5,6,7,8-
tetrahydropyrazolo[3,4-b][1,5]diazepine-1H,4H-5,7-dione. MP: 168°C.
Therapeutic Function
Anxiolytic, Nootropic
Check Digit Verification of cas no
The CAS Registry Mumber 78466-70-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,8,4,6 and 6 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 78466-70:
(7*7)+(6*8)+(5*4)+(4*6)+(3*6)+(2*7)+(1*0)=173
173 % 10 = 3
So 78466-70-3 is a valid CAS Registry Number.
InChI:InChI=1/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
78466-70-3Relevant academic research and scientific papers
Direkte N-Arylierung von Amiden: Eine Verbesserung der Goldberg-Reaktion
Renger, Bernd
, p. 856 - 860 (2007/10/02)
The copper-catalyzed N-arylation of amides, the Goldberg reaction, usually requires drastic reaction conditions and produces only moderate yields of the desired products.Much better results can be achieved by modifying the reaction conditions.We used copper on silica as a catalyst and potassium acetate as a base and continuously removed the resulting acetic acid from the reaction mixture.In this way we gained high, in some cases nearly quantitative yields of the arylated or heteroarylated products.
