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A variety of new pyrazolo[1,5-a]pyrimidines has been prepared as potential drugs for the treatment of insomnia. The general synthetic route used for this purpose involves the condensation of substituted cyanoacetamides 5a-c, prepared by reaction of cyanoacetic acid with amines in presence of acetic anhydride, with dimethylformamide dimethylacetal and subsequent treatment of the formed enamines 6 with hydrazine hydrate. This process affords the corresponding aminopyrazole carboxamides 9 that react with the enaminonitrile 12 to generate the targets. Structures of the substance prepared in these sequences were established by using spectroscopic methods, including N HMBC and NOE difference experiments, as well as X-raycrystallographic analysis.

Synthesis of 7-substituted pyrazolo[1,5-a]pyrimidine-3-carboxamides as potential non benzodiazepine hypnotics