944835-85-2

Basic information

• Product Name: 2-(1H-indazol-6-ylthio)-N-Methyl- BenzaMide
• Synonyms: 2-(1H-indazol-6-ylthio)-N-Methyl- BenzaMide;BenzaMide, 2-(1H-indazol-6-ylthio)-N-Methyl-;Axitinib Impurity e;Axitinib impurity G
• CAS NO: 944835-85-2
• Molecular Formula: C₁₅H₁₃N₃OS
• Molecular Weight: 283.34822
• EINECS: -0
• Mol File: 944835-85-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 555.7±30.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• Storage Temp.: 4°C, Inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• PKA: 13.02±0.40(Predicted)
• CAS DataBase Reference: 2-(1H-indazol-6-ylthio)-N-Methyl- BenzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1H-indazol-6-ylthio)-N-Methyl- BenzaMide(944835-85-2)
• EPA Substance Registry System: 2-(1H-indazol-6-ylthio)-N-Methyl- BenzaMide(944835-85-2)

Safety Data

• Hazardous Substances Data: 944835-85-2(Hazardous Substances Data)

Usage

Description

2-(1H-Indazol-6-ylthio)-N-methylbenzamide is an organic compound that serves as a crucial intermediate in the synthesis of axitinib, an antitumor agent. It is characterized by its unique molecular structure, which includes an indazole ring and a benzamide group, and plays a significant role in the development of cancer treatments.

Uses

Used in Pharmaceutical Industry:
2-(1H-Indazol-6-ylthio)-N-methylbenzamide is used as a key intermediate in the synthesis of axitinib, an antitumor agent, for the treatment of various types of cancer. Its unique molecular structure allows it to be a vital component in the development of effective cancer therapies.
Used in Cancer Treatment:
2-(1H-Indazol-6-ylthio)-N-methylbenzamide is used as a precursor in the production of axitinib, which is an antitumor agent that targets specific pathways involved in tumor growth and angiogenesis. This makes it a valuable compound in the development of targeted cancer therapies, offering potential benefits to patients with various types of cancer.

Upstream product

• 261953-36-0 6-Iodo-1H-indazole 
• 1266386-30-4 6-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 
• 20054-45-9 N-methyl-2-sulfanylbenzamide 
• 119-80-2 2,2'-dithiobenzoic acid 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 6967-12-0 6-amino-1H-indazole 
• 2527-58-4 2,2'-dithiobis(N-methylbenzamide) 

Downstream Products

• 1639137-80-6 N-methyl-2-((1-acetyl-3-((1E)-2-(2-pyridinyl)ethenyl)-1H-indazol-6-yl)thio)benzamide 
• 1639138-00-3 axitinib 
• 319460-85-0 axitinib 
• 885126-34-1 2-((3-iodo-1H-indazol-6-yl)thio)-N-methylbenzamide 

Relevant articles and documents

Safe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C?S Cross-Couplings in Recyclable Water

A new approach to C?S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.

A novel D-glucosamine-derived pyridyltriazole@ palladium catalyst for solvent-free Mizoroki-Heck reactions and its application in the synthesis of Axitinib

A green method for the synthesis of a D-glucosamine-derived triazole@ palladium catalyst is described. The synthesized catalyst containing a 2-pyridyl-1,2,3-triazole ligand was prepared via a click route in high yields and was explored in Heck cross-coupling reactions between different aryl halides and olefins under solventfree conditions. The catalyst can be separated from the reaction mixture and reused at least six times with superior activity. In addition, using this protocol, the marketed drug Axitinib (antitumor) could be synthesized easily.

Methods of preparing indazole compounds

The present invention relates to methods for preparing indazole compounds of formula I, which are useful as modulators and/or inhibitors of protein kinases. The present invention also relates to intermediate compounds useful in the preparation of compounds of formula I.