115930-99-9

Upstream product

• 16617-46-2 3-Amino-4-cyanopyrazole 
• 99-61-6 3-nitro-benzaldehyde 
• 121-44-8 triethylamine 
• 946424-33-5 C₉H₆BrNO₃ 
• 16617-46-2 3-amino-4-cyano-2H-pyrazole 
• 1163721-90-1 3-dimethylamino-1-(3-nitrophenyl)-2-propen-1-one 

Downstream Products

• 1001083-56-2 N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-[²H₅]-ethyl-acetamide 
• 115931-01-6 N-[3-(3-cyano-pyrazolo[1,5-a]pyrimidin-7-yl)phenyl]acetamide 
• 159224-10-9 N-Hydroxy-7-(3-nitro-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxamidine 

Relevant academic research and scientific papers

Preparation method of indinplon intermediate

The invention discloses a preparation method of an indanplon intermediate, and belongs to the technical field of medicinal chemistry. According to the invention, simple and cheap m-nitrobenzaldehyde and triethylamine are adopted as raw materials, and a core skeleton of the indeneplon is efficiently and highly selectively constructed through a one-pot cascade reaction without transition metal catalysis, so that generation of isomers is avoided, generation of byproducts is reduced, the yield of a target product is improved, and the synthesis cost is reduced; and subsequently, simple nitro reduction modification is carried out to prepare the indinplon intermediate. In addition, the reaction condition for preparing the indianplon intermediate is mild, operation is simple and convenient, and the method is suitable for industrial production.

Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment

A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.

Preparation method of zaleplon

The invention discloses a preparation method of zaleplon, and belongs to the technical field of medicinal chemistry. According to the method, m-nitrobenzaldehyde and triethylamine which are simple and cheap are adopted as raw materials, and a core skeleton of zaleplon is efficiently and highly selectively constructed through a one-pot cascade reaction without transition metal catalysis, so that the generation of isomers is avoided, the generation of byproducts is reduced, the yield of a target product is increased, and the synthesis cost is reduced; and simple nitro reduction modification is performed to prepare zaleplon. The whole route is short, reaction conditions are mild, operation is easy and convenient, and the method is suitable for industrial production.

Microwave-assisted palladium mediated efficient synthesis of pyrazolo[3,4-b]pyridines, pyrazolo[3,4-b]quinolines, pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a]quinazolines

An efficient method was developed for the synthesis of pyrazole fused heterocycles via the palladium-catalyzed solvent free reaction of β-halovinyl/aryl aldehydes and 3-aminopyrazoles/5-aminopyrazoles under microwave irradiation in good yields. This method is applicable for the efficient synthesis of a wide range of substituted pyrazolo[3,4-b]pyridines, pyrazolo[3,4-b]quinolines, pyrazolo[1,5-a]pyrimidines and pyrazolo[1,5-a] quinazolines. Four of the synthesized pyrazole fused compounds showed in vitro cytotoxic activities almost comparable to the drug doxorubicin against the cervical HeLa cancer cell line and prostate DU 205 cancer cell line. The Royal Society of Chemistry 2014.

Synthesis of deuterium-labeled zaleplon-d5 as an internal standard

Zaleplon is licensed for the short-term treatment of insomnia. Excessive usage causes side effects; hence, the drug is controlled. Identifying zaleplon in a drug abuser requires an isotope-labeled internal standard. This work presents a synthesis of stable isotope-labeled internal standard for zaleplon, zaleplon-d5, by a five-step synthetic sequence. Copyright

4,5-dihydro and 4,5,6,7-tetrahydropyrazolo(1,5-A)-pyrimidines

Novel compounds having the following structural formula: STR1 wherein - - - may represent the presence of a double bond between the C6 and C7 position, Ia, or the absence of a double bond between the C6 and C7 position, Ib; R1 is selected from the group consisting essentially of hydrogen, bromo, chloro, carbamoyl, carboxyl, carboxyalkoxyl where alkoxyl is (C1 -C3), cyano, --CO--CF3, COONa, STR2 --CO--C(CH3)3, and STR3 where X is hydrogen, cyano, halogen and nitro; R2, R4 and R5 may be hydrogen and lower alkyl (C1 -C3); R3 is hydrogen, alkyl (C1 -C3), STR4 where R7 and R8 may be the same or different and are selected from the group consisting essentially of hydrogen, halogen, alkyl (C1 -C3), nitro, alkoxy (C1 -C3), trifluoro-methyl, acetylamino or N-alkylacetylamino where alkyl is (C1 -C3), and R3 may also be selected from a monovalent radical selected from the class consisting essentially of 3-thienyl, 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, either of said pyridinyl radicals being optionally substituted with an alkyl radical R9, where alkyl is (C1 -C4), and the structures of the monovalent 2-pyridinyl, 3-pyridinyl and 4-pyridinyl moieties are depicted respectively as: STR5 R6 is hydrogen or alkyl-(C1 -C3); pharmaceutical compositions of matter containing the above-defined compounds; methods for using the compounds as anxiolytic agents, antihypertensive agents or antidepressant agents in mammals; processes for the preparation of the compounds.