63365-17-3

Basic information

• Product Name: 2-Amino-6-(4-methyl-1-piperazinyl)benzonitrile
• Synonyms: 2-Amino-6-(4-methyl-1-piperazinyl)benzonitrile
• CAS NO: 63365-17-3
• Molecular Formula: C₁₂H₁₆N₄
• Molecular Weight: 216
• Mol File: 63365-17-3.mol

Chemical Properties

• Melting Point: 151-154℃
• Boiling Point: 425.1°C at 760 mmHg
• Flash Point: 210.9°C
• Appearance: /
• Density: 1.20
• Vapor Pressure: 1.97E-07mmHg at 25°C
• Refractive Index: 1.628
• PKA: 7?+-.0.42(Predicted)
• CAS DataBase Reference: 2-Amino-6-(4-methyl-1-piperazinyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-(4-methyl-1-piperazinyl)benzonitrile(63365-17-3)
• EPA Substance Registry System: 2-Amino-6-(4-methyl-1-piperazinyl)benzonitrile(63365-17-3)

Safety Data

• Hazardous Substances Data: 63365-17-3(Hazardous Substances Data)

Usage

Class

Benzonitrile
Derivative of piperazine
Amino group at 2-position
Piperazine group at 6-position of benzene ring
Potential pharmaceutical properties
Use as intermediate in synthesis of pharmaceuticals
Building block for production of various drugs
Suitable for medicinal chemistry and drug development
Handle and store with caution due to potential risks to human health and environment

InChI:InChI=1/C12H16N4/c1-15-5-7-16(8-6-15)12-4-2-3-11(14)10(12)9-13/h2-4H,5-8,14H2,1H3

Upstream product

• 63365-16-2 2-(4-methylpiperazinyl)-6-nitrobenzenecarbonitrile 
• 109-01-3 1-methyl-piperazine 
• 35213-00-4 2,6-dinitrobenzonitrile 

Downstream Products

• 77245-52-4 1-(4-Methoxy-benzyl)-1H-tetrazole-5-carboxylic acid [2-cyano-3-(4-methyl-piperazin-1-yl)-phenyl]-amide 
• 405169-01-9 4-amino-3-benzimidazol-2-yl-5-(4-methylpiperazinyl)hydroquinolin-2-one 

Relevant articles and documents

Design, structure-activity relationships and in vivo characterization of 4-Amino-3-benzimidazol-2-ylhydroquinolin-2-ones: Novel class of receptor tyrosine kinase inhibitors

The inhibition of key receptor tyrosine kinases (RTKs) that are implicated in tumor vasculature formation and maintenance, as well as tumor progression and metastasis, has been a major focus in oncology research over the last several years. Many potent small molecule inhibitors of vascular endothelial growth factor receptor (VEGFR) and platelet-derived growth factor receptor (PDGFR) kinases have been evaluated. More recently, compounds that act through the complex inhibition of multiple kinase targets have been reported and may exhibit improved clinical efficacy. We report herein a series of potent, orally efficacious 4-amino- 3-benzimidazol-2-ylhydroquinolin-2-one analogues as inhibitors of VEGF, PDGF, and fibroblast growth factor (FGF) receptor tyrosine kinases. Compounds in this class, such as 5 (TKI258), are reversible ATP- competitive inhibitors of VEGFR-2, FGFR-1, and PDGFRβ with IC50 values 0.1 μM. On the basis of its favorable in vitro and in vivo properties, compound 5 was selected for clinical evaluation and is currently in phase I clinical trials.

N-(Aminophenyl)oxamic Acids and Esters as Potent, Orally Active Antiallergy Agents

A series of N-(2-cyano-substituted-phenyl)oxamates was prepared by acylation of the appropriate anthranilonitrile with ethyloxalyl chloride.Hydrolysis with sodium hydroxide gave the corresponding oxamic acid sodium salts.These compounds were extremely potent when tested in the rat passive cutaneous anaphylaxis (PCA assay either by the ip or the po route of administration).One of the sodium salts, oxoacetic acid sodium salt (11a, Wy-41 195), has ED50 value of 0.07 mg/kg po and has been selected for further evaluation.