1820-80-0

Usage

Uses

Used in Pharmaceutical Industry:
3-Aminopyrazole is used as a key intermediate for the synthesis of heterocyclic compounds that hold significant pharmaceutical value. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
3-Aminopyrazole is employed in a one-pot synthesis of pyrazolopyrimidines, which are important scaffolds in medicinal chemistry.
Used in Spectroscopic Characterization:
3-Aminopyrazole was utilized in the spectroscopic characterization of ferrocenoyl peptides via 1H-NMR spectroscopy, providing valuable insights into the structure and properties of these compounds.
Used in Condensation Reactions:
3-Aminopyrazole is used in the synthesis of symmetrical dialkylpyrazolo[1,5-a]pyrimidines via condensation with symmetrical β-diketones, contributing to the development of novel heterocyclic compounds.
Used in the Synthesis of 4-Annelated Coumarins:
3-Aminopyrazole is involved in the synthesis of 4-annelated coumarins, which are heterocyclic compounds with potential applications in various fields, including pharmaceuticals and materials science.
Used in the Preparation of Hetrocyclic Compounds of Pharmaceutical Interest:
3-Aminopyrazole is used in the preparation of heterocyclic compounds with potential pharmaceutical applications, showcasing its importance as a building block in the development of new drugs.

Synthesis

The synthesis of?3-Aminopyrazole is as follows:A solution of 50 mg (0.34 mmol) of 3-oxo-3-phenylpropanenitrile and 11.6 mg (0.36 mmol) of hydrazine and 0.024 mL of acetic acid (0.37 mmol) in 3 mL of anhydrous ethanol was heated at 60° C for 24 hr. The mixture was cooled to ambient temperature and the solvent removed in vacuo. The residue was taken up in ethyl acetate, washed with saturated sodium bicarbonate. The organic layer was washed with brine and dried over MgSO4, filtered and evaporated. The solid residue waswashedwithethyl ether and dried in vacuo to give 45 mg (82%) of 3-phenyl-1H-pyrazol-5-amine.

InChI:InChI=1/C3H5N3/c4-3-1-2-5-6-3/h1-2H,(H3,4,5,6)

Upstream product

• 41680-34-6 3-aminopyrazole-4-carboxylic acid 
• 871-29-4 trans-β-chloroacrylonitrile 
• 26621-44-3 3-nitro-1H-pyrazole 
• 6162-76-1 cyanoacetaldehyde 

Downstream Products

• 29274-35-9 5-methyl-4H-pyrazolo<1,5-a>pyrimidin-7-one 
• 99898-82-5 5-(p-nitrophenyl)pyrazolo<1,5-a>pyrimidin-7-one 
• 29274-23-5 4,7-dihydropyrazolo<1,5-a>pyrimidin-7-one 
• 61578-01-6 7-Methylpyrazolo<1,5-a>pyrimidine 
• 61578-03-8 5-Methyl-pyrazolo<1,5-a>pyrimidin 
• 130506-80-8 6-acetyl-7-methylpyrazolo<1,5-a>pyrimidine 
• 84397-45-5 C₁₈H₂₀N₆O₅ 
• 99898-81-4 5-(p-chlorophenyl)pyrazolo<1,5-a>pyrimidin-7-one 
• 96799-09-6 2-Phenyl-4-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a][1,3,5]triazine 
• 96799-12-1 2-(4-Chloro-phenyl)-4-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a][1,3,5]triazine 
• 109013-31-2 3-Amino-N-phenyl-1H-pyrazol-1-carboxamid 
• 109013-09-4 3-Phenyl-pyrazolo<5,1-d>-1,2,3,5-tetrazin-4(3H)-on 
• 134242-03-8 2,2-Dimethyl-4-phenoxy-2,3-dihydro-pyrazolo<1,5-a>-s-triazin 
• 134242-02-7 5-Amino-pyrazol-1-imidsaeurephenylester 

Relevant academic research and scientific papers

Synthesis of aminopyrazole analogs and their evaluation as CDK inhibitors for cancer therapy

We synthesized a library of aminopyrazole analogs to systematically explore the hydrophobic pocket adjacent to the hinge region and the solvent exposed region of cyclin dependent kinases. Structure-activity relationship studies identified an optimal substitution for the hydrophobic pocket and analog 24 as a potent and selective CDK2/5 inhibitor.

ADENOSINE A3 RECEPTOR MODULATING COMPOUNDS AND METHODS OF USE THEREOF

Provided herein is a method of preventing, treating, or ameliorating one or more symptoms of an adenosine A3-mediated condition, disorder, or disease, with a compound of Formula I. Also provided herein is a method of preventing, treating, or ameliorating one or more symptoms of glaucoma or ocular hypertension. Further provided herein is a method of modulating the activity of an adenosine A3 receptor.

Rapid reduction of heteroaromatic nitro groups using catalytic transfer hydrogenation with microwave heating

A method for the rapid, safe reduction of heteroaromatic and aromatic nitro groups to amines is described using catalytic transfer hydrogenation under microwave heating conditions. Commonly available Pd/C or Pt/C catalyst is extremely effective with 1,4-cyclohexadiene as the hydrogen transfer source. In the case of substrates containing potentially labile aromatic halogens, Pt/C is effective and results in little or no dehalogenation. In general, the reactions are complete within 5 min at 120 °C.

Heterocyclic dihydropyrimidine compounds

Novel heterocyclic dihydropyrimidine compounds useful as inhibitors of potassium channel function (especially inhibitors of the Kv1 subfamily of voltage gated K+ channels, especially inhibitors Kv1.5 which has been linked to the ultra-rapidly activating delayed rectifier K+ current IKur), methods of using such compounds in the prevention and treatment of arrhythmia and IKur-associated conditions, and pharmaceutical compositions containing such compounds.

Methods of treating cytokine mediated diseases

Disclosed are methods of treating certain cytokine mediated diseases or conditions using novel aromatic heterocyclic compounds of the formula(I) wherein Ar1,Ar2,L,Q and X are described herein.

Aromatic heterocyclic compounds as antiinflammatory agents

Disclosed are novel aromatic heterocyclic compounds of the formula(I) wherein Ar1,Ar2,L,Q and X are described herein. The compounds are useful in pharmaceutic compositions for treating diseases or pathological conditions involving inflammation such as chronic inflammatory diseases. Also disclosed are processes of making such compounds.

3-(heteroarylamino)methylene-1,3-dihydro-2H-indol-2-ones as kinase inhibitors

The present invention relates to organic molecules capable of modulating tyrosine kinase signal transduction in order to regulate, modulate and/or inhibit abnormal cell proliferation.

Aminopyrazoles. IV. Pyrazol-3- and 5-amines from 2,3-dihaloalkanenitriles or 3-Chloroacrylonitriles and Hydrazines

2,3-Dihalopropanenitriles and substituted 3-chloropropenenitriles react with hydrazines in basic solution to form either pyrazol-3-amines 4 or pyrazol-5-amines 5 or a mixture of both isomers.