【药物名称】SR-265579, WIN-65579
化学结构式(Chemical Structure):
参考文献No.23298
标题:6-Heterocyclyl pyrazolo[3,4-d]pyrimidin-4-ones and compsns. and method of use
作者:Bacon, E.R.; Singh, B.; Lesher, G.Y.; Lesher, L.E. (Sanofi-Synth閘abo)
来源:US 5294612
合成路线图解说明:

Reaction of triethyl orthopropionate (I) with malononitrile (II) at reflux temperature provided (1-ethoxypropylidene)malononitrile (III). Cyclopentanone (IV) was condensed with tert-butyl carbazate (V) to afford the corresponding hydrazone (VI). Subsequent reduction with sodium cyanoborohydride, followed by acid deprotection furnished cyclopentylhydrazine (VII). Then, condensation of (VII) with malononitrile derivative (III) produced pyrazole (VIII). Partial hydrolysis of the cyano group of (VIII) using concentrated sulfuric acid gave carboxamide (IX).

合成路线图解说明:

Treatment of 4-cyanopyridine N-oxide (X) with phosphorus oxychloride and phosphorus pentachloride under reflux produced a mixture of 2-chloro (XI) and 3-chloropyridines (XII), which were separated by column chromatography. The 3-chloro isomer (XII) was further treated with sodium ethoxide in DMF to produce the ethoxypyridine (XIII). The pyrazolopyrimidine nucleus (XIV) was then obtained by condensation of cyanopyridine (XIII) with aminopyrazole (IX) in the presence of NaH. Finally, diazotization of (XIV) in 50% sulfuric acid converted the aminopyrimidine group into the required pyrimidinone.

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