16459-47-5

Usage

Uses

Used in Pharmaceutical Research and Development:
5-METHYL-2-(4-NITROPHENYL)-2H-PYRAZOL-3-YLAMINE is used as a building block for the synthesis of bioactive compounds in the pharmaceutical industry. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-METHYL-2-(4-NITROPHENYL)-2H-PYRAZOL-3-YLAMINE is used as a key intermediate for the production of various chemical compounds. Its versatility in chemical reactions makes it a valuable component in the synthesis of pharmaceuticals and other related compounds.
Used in Chemical Research:
5-METHYL-2-(4-NITROPHENYL)-2H-PYRAZOL-3-YLAMINE is also utilized in chemical research for studying its properties and potential applications. Its unique structure and reactivity make it an interesting subject for further exploration and development in the chemical sciences.

InChI:InChI=1/C10H10N4O2/c1-7-6-10(11)13(12-7)8-2-4-9(5-3-8)14(15)16/h2-6H,11H2,1H3

Upstream product

• 2469-99-0 Cyanoaceton 
• 100-16-3 4-nitrophenylhydrazone 
• 1118-61-2 3-Aminocrotononitrile 
• 619-27-2 3-nitrophenylhydrazine 
• 100-01-6 4-nitro-aniline 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 

Downstream Products

• 1172134-99-4 4-(4-chlorophenyl)-3-methyl-1-(4-nitrophenyl)-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidine-5,7(6H,8H)-dione 
• 77746-99-7 N,N-Dimethyl-N'-[5-methyl-2-(4-nitro-phenyl)-4-(phenyl-hydrazonomethyl)-2H-pyrazol-3-yl]-formamidine 
• 77747-01-4 C₁₅H₁₈N₈O₃ 
• 77746-61-3 N'-[4-Formyl-5-methyl-2-(4-nitro-phenyl)-2H-pyrazol-3-yl]-N,N-dimethyl-formamidine 
• 77746-78-2 N,N-Dimethyl-N'-[5-methyl-2-(4-nitro-phenyl)-2H-pyrazol-3-yl]-formamidine 
• 116835-06-4 1-(2,4-Dinitro-phenyl)-3-methyl-5-nitro-1H-pyrazolo[3,4-b]pyridine 
• 116835-05-3 1-(2,4-Dinitro-phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine 
• 444794-36-9 3-(2-hydroxy-5-chlorobenzoyl)-5-methyl-7-(4-nitrophenyl)pyrazolo[3,4-b]pyridine 

Relevant academic research and scientific papers

Microwave synthesis of 1-aryl-1H-pyrazole-5-amines

A microwave-mediated synthesis of 1H-pyrazole-5-amines utilizing 1 M HCl at 150 °C was developed in order to provide products in a matter of minutes with minimal purification. Most reactions are complete in only 10 min and can be isolated via a simple filtration without the need for further purification by column chromatography or recrystallization. This method tolerates a range of functional groups and can be performed on milligram to gram scales.

Efficient catalyst-free tricomponent synthesis of new spiro[cyclohexane-1,4′-pyrazolo[3,4-e][1, 4]thiazepin]-7′(6′H)-ones

A series of spirocyclohexane-1,4′-pyrazolothiazepinones were synthesized by one-pot multicomponent cyclocondensation reactions between 5-amino-1-arylpyrazoles, cyclohexanone and mercaptoacetic acid with good yields and easy purification protocols. Some control experiments involving isolation of reaction intermediates were performed leading to the proposal of three alternative mechanistic pathways conducting to the named spiroheterocycles. All target molecules were fully characterized by IR, NMR, melting point and HRMS.

One-pot, telescoped synthesis of N-aryl-5-aminopyrazoles from anilines in environmentally benign conditions

An efficient synthetic approach to synthesize N-aryl-5-aminopyrazoles from anilines via a one-pot, telescoped reaction performed in entirely aqueous conditions has been developed. This protocol provides a rapid, convenient method to prepare N-aryl-5-aminopyrazoles, useful building blocks for the synthesis of several bicyclic nitrogen heterocycles, by avoiding the isolation of the toxic intermediate arylhydrazines and the use of a metallic reductant. The Royal Society of Chemistry 2014.

NEW POSITIVE ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTOR

The present invention relates to compounds useful in therapy, to compositions comprising said compounds, and to methods of treating diseases comprising administration of said compounds. The compounds referred to are positive allosteric modulators (PAMs) of the nicotinic acetylcholine alpha7 receptor.

PYRAZOLOPYRIDINES USEFUL IN THE TREATMENT OF DISORDERS OF THE CENTRAL NERVOUS SYSTEM

The present invention relates to compounds useful in therapy, to compositions comprising said compounds, and to methods of treating diseases comprising administration of said com- pounds. The compounds referred to are positive allosteric modulators (PAMs) of the nicotinic acetylcholine α7 receptor.

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.