72583-83-6

Basic information

• Product Name: 1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE
• Synonyms: 1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE;1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE;1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine ,97%;3-amino-1-methylpyrazolopyridine;1-Methyl-3-aMino-1H-pyrazolo[3,4-b]pyridine;1-Methyl-1H-pyrazolo[3,4-b]pyridin-3-ylaMine (en)
• CAS NO: 72583-83-6
• Molecular Formula: C₇H₈N₄
• Molecular Weight: 148.17
• Mol File: 72583-83-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 104-106°C
• Boiling Point: 340.713 °C at 760 mmHg
• Flash Point: 159.858 °C
• Appearance: /
• Density: 1.422 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.728
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 5.31±0.30(Predicted)
• CAS DataBase Reference: 1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE(72583-83-6)
• EPA Substance Registry System: 1-METHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-YLAMINE(72583-83-6)

Safety Data

• Hazard Codes: T
• Statements: 25-36-36/37/38-22
• Safety Statements: 26-45-36/37/39-22
• HazardClass: IRRITANT
• Hazardous Substances Data: 72583-83-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow solid

InChI:InChI=1/C7H8N4/c1-11-7-5(6(8)10-11)3-2-4-9-7/h2-4H,1H3,(H2,8,10)

Upstream product

• 14906-64-0 3-cyanopyridine N-oxide 
• 1060802-53-0 3-cyano-4-fluoropyridine 
• 60-34-4 methylhydrazine 
• 6602-54-6 2-chloro-3-pyridinecarbonitrile 

Downstream Products

• 1345014-85-8 4-[(1-methyl-1H-pyrazolo[3,4-b]pyridin-3-yl)amino]-2-phenyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one 
• 685522-76-3 3-iodo-1-methyl-1H-pyrazolo[3,4-b]pyridine 
• 116855-03-9 3-bromo-1-methyl-pyrazolo[3,4-b]pyridine 
• 116855-06-2 3-Chloro-1-methyl-1H-pyrazolo[3,4-b]pyridine 
• 116834-95-8 1-methyl-3-phenyl-pyrazolo<3,4-b>pyridine 

Relevant articles and documents

A general, one-step synthesis of substituted indazoles using a flow reactor

Flow chemistry is a rapidly emerging technology within the pharmaceutical industry, both within medicinal and development chemistry groups. The advantages of flow chemistry, increased safety, improved reproducibility, enhanced scalability, are readily apparent, and we aimed to exploit this technology in order to provide small amounts of pharmaceutically interesting fragments via a safe and scalable route, which would enable the rapid synthesis of multigram quantities on demand. Here we report a general and versatile route which utilises flow chemistry to deliver a range of known and novel indazoles, including 3-amino and 3-hydroxy analogues.

Synthesis and antibacterial activity of 1H-pyrazolo[3,4-b]pyrazine and -pyridine derivatives

The investigations of new pyrazine and pyridine derivatives showing an antibacterial activity have been made. Upon treatment of 3-chloro-2- cyanopyrazine [1] and 2-chloro-3-cyanopyridine with 1,1-dimethyl-hydrazine, 1-aminopiperidine and 1-amino-4-methylpiperazine, either the pyrazolo-pyrazine (1), and -pyridine (2) derivatives, or ammonium salts (3-8) were obtained, according to the reaction conditions. Compound 1 was obtained in the reaction of the initial nitrile with methylhydrazine as well. The reactions of 1 gave the following derivatives: acylation - (9), that with p-chlorobenzoic aldehyde-(10), and with phenyl-isothiocyanate - (11). 3-Chloro-2-cyanopyrazine treated with hydrazine hydrate gave amidrazone (12), which upon condensation with p-chlorobenzoic aldehyde produced (13). The compounds obtained were tested in vitro for their tuberculostatic activity. The minimal inhibitory concentration (MIC) values were within 22-100 μ g/cm3. Compounds 1, 5 and 6 were also tested in vitro for their activity towards 25 strains of anaerobic, and 25 strains of aerobic bacteria. They appeared to be of elevated activity towards the anaerobes and of low one towards the aerobes (Table 2).

Pyrazolo[3,4-b]pyridines: Syntheses, reactions, and nuclear magnetic resonance spectra

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