【药物名称】UC-781
化学结构式(Chemical Structure):
参考文献No.33529
标题:Furan- and thiophenecarbothioamide derivs., their preparation and their use as inhibitors of the replication of HIV-1 and HIV-1 mutants
作者:Brouwer, W.G.; Osika, E.M.; Pierce, B.J. (Uniroyal Chemical Company, Inc.)
来源:EP 0874839; JP 1999504657; US 5696151; WO 9719940
合成路线图解说明:

The diazonium salt prepared from 2-amino-5-nitrophenol (I) was subjected to Sandmeyer reaction in the presence of HCl and CuCl to afford the chlorophenol derivative (II). Subsequent alkylation of phenol (II) with prenyl bromide (III) produced ether (IV). Amine (V) was then obtained by reduction of the nitro group of (IV) employing iron powder in the presence of HCl.

合成路线图解说明:

Chloroacetaldehyde (VII), prepared by acid hydrolysis of the dimethyl ketal (VI), was condensed with ethyl acetoacetate (VIII) to produce ethyl 2-methyl-3-furoate (IX). Basic hydrolysis of ester (IX), followed by chlorination of the resultant carboxylic acid (X) with SOCl2, gave acid chloride (XI). Then, condensation of amine (V) with acid chloride (XI) yielded amide (XII), which was finally converted to the title thioamide by treatment with Lawesson's reagent in hot toluene.

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