64664-15-9

Upstream product

• 1131-18-6 1-Phenyl-3-methyl-5-aminopyrazole 
• 98-88-4 benzoyl chloride 
• 633336-56-8 C₁₉H₂₀N₃O₃P 
• 69730-13-8 2-amino-N-methyl-N-(3-methyl-1-phenyl-1H-pyrazol-5-yl)benzamide 
• 215545-42-9 C₁₈H₁₆N₅O⁽¹⁺⁾*HO₄S^(1-) 
• 100-63-0 phenylhydrazine 
• 633336-22-8 1-bromo-7-methyl-3,5-diphenyl-1,5-dihydropyrazolo[4,3-c][1,5,2]oxazaphosphinine 
• 633336-25-1 3-methyl-1-phenyl-5-phenylcarboxamido-1H-4-pyrazolylphosphinic acid 
• 633336-32-0 methyl(3-methyl-1-phenyl-5-phenylcarboxamido-1H-pyrazolyl)phosphonite 

Downstream Products

• 633336-45-5 dimethyl-[4-(3-methyl-1,6-diphenyl-1H-5-oxa-1,2,7-triaza-4-phospha-inden-4-yl)-phenyl]-amine 
• 633336-24-0 7-methyl-1,3,5-triphenyl-1,5-dihydropyrazolo[4,3-c][1,5,2]oxazaphosphinine 
• 633336-22-8 1-bromo-7-methyl-3,5-diphenyl-1,5-dihydropyrazolo[4,3-c][1,5,2]oxazaphosphinine 
• 633336-54-6 4-methoxy-3-methyl-1,6-diphenyl-1,4-dihydro-5-oxa-1,2,7-triaza-4-phospha-indene 
• 633336-55-7 3-methyl-4-phenoxy-1,6-diphenyl-1,4-dihydro-5-oxa-1,2,7-triaza-4-phospha-indene 
• 633336-47-7 3-methyl-4-morpholin-4-yl-1,6-diphenyl-1,4-dihydro-5-oxa-1,2,7-triaza-4-phospha-indene 
• 633336-51-3 (3-methyl-4-morpholin-4-yl-1,6-diphenyl-1,4-dihydro-5-oxa-1,2,7-triaza-4λ⁵-phospha-inden-4-ylidene)-phenyl-amine 
• 633336-59-1 (3-chloro-4-methyl-phenyl)-(3-methyl-1,4,6-triphenyl-1,4-dihydro-5-oxa-1,2,7-triaza-4λ⁵-phospha-inden-4-ylidene)-amine 
• 105438-77-5 N-benzyl-3-methyl-1-phenyl-1H-pyrazol-5-amine 

Relevant academic research and scientific papers

Non-classical transformation of benzendiazonium hydrogen sulfates. access to 1,3-dimethylisochromeno[4,3-c]pyrazol-5(1h)-one, a potential benzodiazepine receptor ligand

The compound 2-((1,3-dimethyl-1H-pyrazol-5-yl)(methyl)carbamoyl) benzenediazonium hydrogen sulfate (10) was reacted with copper sulfate and sodium chloride, in the presence of ascorbic acid as reducing agent, to afford a mixture of the chlorinated epimers 4′-chloro-2,2′,5′- trimethyl-2′,4′-dihydrospiro[isoindoline-1,3′-pyrazol]-3-one (18) and (19), the epimers 4′-hydroxy-2,2′,5′-trimethyl- 2′,4′-dihydrospiro[isoindoline-1,3′- pyrazol]-3-one (20) and (21), and N-(1,3-dimethyl-1H-pyrazol-5-yl)benzamide (22). Under the foregoing conditions, diazonium salt 10 affords neither the 2-chloro-N-(1,3-dimethyl- 1H-pyrazol-5-yl)-N-methylbenzamide (23) nor the tricyclic derivative 24, the classical products of the Sandmeyer and Pschorr reactions, respectively. Finally, by heating 20 at 210 °C the compound 1,3-dimethylisochromeno[4,3-c] pyrazol-5(1H)-one (24) was obtained. The transformation under the above conditions of 2-((4-chloro-3-methyl-1-phenyl- 1H-pyrazol-5-yl)(methyl)carbamoyl) benzendiazonium hydrogen sulphate (11) afforded 4′,4′-dichloro-2, 5′-dimethyl-2′-phenyl-2′,4′-dihydrospiro[isoindoline-1, 3′-pyrazol]-3-one (29) as the sole reaction product.

Structure-activity relationship and improved hydrolytic stability of pyrazole derivatives that are allosteric inhibitors of West Nile Virus NS2B-NS3 proteinase

West Nile Virus (WNV) is a potentially deadly mosquito-borne flavivirus which has spread rapidly throughout the world. Currently there is no effective vaccine against flaviviral infections. We previously reported the identification of pyrazole ester derivatives as allosteric inhibitors of WNV NS2B-NS3 proteinase. These compounds degrade rapidly in pH 8 buffer with a half life of 1-2 h. We now report the design, synthesis and in vitro evaluation of pyrazole derivatives that are inhibitors of WNV NS2B-NS3 proteinase with greatly improved stability in the assay medium.

One-pot synthesis of (5-aminopyrazol-4-yl)-phosphonic acid derivatives from 1-aryl-5-arylcarboxamidopyrazoles through pyrazolo[4,3-c][1,5,2]-oxazaphosphinines

1-Aryl-5-arylcarboxamidopyrazoles react with phosphorus(III) halides giving the new heterocyclic system: pyrazolo[4,3-c][1,5,2]oxazaphosphinine. Treatment of pyrazolo[4,3-c][1,5,2]oxazaphosphinines with nucleophilic or electrophilic reagents leads to a cleavage of the oxazaphosphinine ring yielding derivatives of (5-aminopyrazol-4-yl)phosphonic acid.

One-step synthesis, crystallographic studies and antimicrobial activity of new 4-diazopyrazole derivatives

A number of new 4-diazopyrazole derivatives were prepared by the reaction of 1-R-3-methyl-5(R1-substituted)benzamidopyrazoles with a sevenfold excess of nitrous acid in acetic medium. The compounds were tested for activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus faecalis, Listeria monocytogenes, Candida albicans, Candida tropicalis and Paecilomyces varioti. The highest microbial susceptibility was shown by Gram-positive bacteria, with minimum inhibitory concentrations (MIC) in the range 0.5-12.5 μg/mL. For S aureus the R1 substituents were screened utilizing the Topliss operational scheme. The 4-nitro group was found to be the best substituent. We also tested the compounds 41,o,p, found to be the most active in the test against S aureus ATCC 25923, on ten clinical S aureus strains, five of which were sensitive and five resistant to methicillin. The above compounds were active in the range 2-8 μg/mL against methicillin-resistant S aureus strains. An X-ray analysis of compounds 4i and 4q is reported.

A NEW ROUTE TO THE SYNTHESIS OF IMIDAZOPYRAZOLES

A new synthesis of imidazopyrazoles, obtained through cyclisation of 4-nitroso-5-alkylamino-pyrazoles, is described.

VILSMEIER-HAACK REACTION OF 5-AMINO- AND 5-ACYLAMINO-PYRAZOLES

The Vilsmeier-Haack reaction of 5-aminopyrazole derivatives 1 was investigated in view of contradictory literature reports.Structure 2 of the products was proved both chemically and spectroscopically.The mechanism of the reaction was postulated on the basis of isolated intermediates 7 and 8. 5-Acylaminopyrazoles 9, 10 and 11 were found to give also 2 (and 7) under the Vilsmeier conditions by an acyl splitting reaction, proceeding probably via diacylamino derivatives 12.Compounds 2 provided a simple route to pyrazolopyrimidine derivatives 13 and 14 as well as to azomethine compounds 15-18.