93764-93-3

Usage

Uses

Ethyl 5-amino-4-cyano-1-phenylpyrazole-3-carboxylate

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 21, p. 1049, 1984 DOI: 10.1002/jhet.5570210425

InChI:InChI=1/C13H12N4O2/c1-2-19-13(18)11-10(8-14)12(15)17(16-11)9-6-4-3-5-7-9/h3-7H,2,15H2,1H3

Upstream product

• 28663-68-5 ethyl (phenylhydrazono)chloroacetate 
• 109-77-3 malononitrile 
• 59-88-1 phenylhydrazine hydrochloride 
• 80447-71-8 phenylhydrazone of ethyl ester of glyoxalic acid 
• 1649463-17-1 ethyl 5-azido-4-cyano-1-phenyl-1H-pyrazole-3-carboxylate 
• 1649463-16-0 ethyl 5-chloro-4-cyano-1-phenyl-1H-pyrazole-3-carboxylate 
• 38405-71-9 ethyl 5-chloro-4-formyl-1-phenyl-1H-pyrazolo-3-carboxylate 
• 28663-68-5 ethyl chloro(2-phenylhydrazono)acetate 
• 28663-68-5 ethyl 2-chloro-2-(2-phenylhydrazono)acetate 

Downstream Products

• 152992-76-2 4-Oxo-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid 
• 1015765-52-2 ethyl 4-cyano-1-phenyl-5-(1H-pyrol-1-yl)-1H-pyrazole-3-carboxylate 
• 201735-21-9 ethyl 5-amino-4-carbamoyl-1-phenyl-1H-pyrazole-3-carboxylate 
• 1649463-19-3 ethyl 5-amino-4-imino-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-20-6 5-amino-4-imino-1-phenyl-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidine-3-carbohydrazide 
• 1649463-22-8 ethyl 4,5-dihydro-6-(3,4-dimethoxyphenyl)-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-23-9 ethyl 4,5-dihydro-6-(3-methoxyphenyl)-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-24-0 ethyl 6-(4-chlorophenyl)-4,5-dihydro-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-25-1 ethyl 4,5,6,7-tetrahydro-6-(3,4-dimethoxyphenyl)-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-26-2 ethyl 4,5,6,7-tetrahydro-6-(3-methoxyphenyl)-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 1649463-27-3 ethyl 6-(4-chlorophenyl)-4,5,6,7-tetrahydro-4-oxo-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylate 
• 93745-28-9 1-Phenyl-4,6-dithioxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-d]pyrimidine-3-carboxylic acid ethyl ester 
• 93745-34-7 2-Phenyl-2,3,5,7-tetrahydro-1,2,3,5,6,7-hexaaza-acenaphthylene-4,8-dione 
• 152992-89-7 (8-Oxo-2-phenyl-2,3,7,8-tetrahydro-1,2,3,5,6,7-hexaaza-acenaphthylen-4-ylsulfanyl)-acetic acid 

Relevant academic research and scientific papers

Palladium and Copper Cocatalyzed Intermolecular Cyclization Reaction: Synthesis of 5-Aminopyrazole Derivatives

A novel and efficient palladium and copper co-catalyzed intermolecular cyclization of acetonitriles with hydrazones has been developed for the synthesis of 5-aminopyrazoles through C-C and C-N bond formation. The reaction has the advantages of easily avai

New synthesis and reactions of ethyl 5-amino-4-cyano-1-phenyl-1H-pyrazole- 3-carboxylate

Synthesis of ethyl 5-amino-4-cyano-1-phenyl-1H-pyrazole-3-carboxylate 5 has been achieved via abnormal Beckmann rearrangement of o-chloroaldehyde 1. Reaction of o-aminocarbonitrile 5 with concentrated H2SO4 furnished expected o-amino

Synthesis, cannabinoid receptor affinity, and molecular modeling studies of substituted 1-aryl-5-(1H-pyrrol-1-yl)-1H-pyrazole-3-carboxamides

The new 1-phenyl-5-(1H-pyrrol-1-yl)pyrazole-3-carboxamides were compared with the reference compounds AM251 and SR144528 for cannabinoid hCB1 and hCB2 receptor affinity. Compounds bearing 2,4-dichlorophenyl or 2,4-difluorophenyl groups at position 1 and 2,5-dimethylpyrrole moiety at position 5 of the pyrazole nucleus were generally more selective for hCB 1. On the other hand, the N-cyclohexyl group at the 3-carboxamide was the determinant for the hCB2 selectivity, in particular when a 3,4-dichlorophenyl group was also present at position 1. Compound 26 was the most selective ligand for the hCB1 receptor (Ki (CB 2)/Ki (CB1) = 140.7). Derivative 30, the most potent hCB1 ligand (Ki = 5.6 nM), was equipotent to AM251 and behaved as an inverse agonist in the cAMP assay (EC50 ～1 nM). The carbonyl oxygen of both 26 and 30 formed a H-bond with K3.28(192), while the substituents at the nitrogen fitted in a pocket formed by lipophilic residues. This H-bonding interaction was proposed to account for the high affinity for receptors' inactive state and the inverse agonist activity.

Heterocyclic Synthesis Using Hydrazonoyl Halides: Synthesis of Annelated Pyrimidines, Pyridazines and Pyrazoles

Aminocyanopyrazoles and dihydropyrrolopyrazole-4,6-diones were obtained in good yields by the reaction of hydrazonoyl halides with malononitrile and N-arylmaleimides respectively. Pyrazolopyrimidines and pyrazolopyridazines were synthesized in quantitative yields by the reaction of formic acid or formamide and hydrazine hydrate with aminocyanopyrazoles. Novel ring systems, 4-mercapto-1,2,3,5,6,7-hexaazaacenaphthylenes 20 and 7-thia-1,2,4,5,6,10-hexaazacyclopentacenaphthylenes 22 were prepared by the reaction of 18 with carbon disulfide and the reaction of 21 with acetic anhydride. The structures of the products were assigned and confirmed on the basis of their elemental analyses, spectral data and alternate synthesis wherever possible.