885126-35-2

Basic information

• Product Name: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide
• Synonyms: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide;6-(2-mercapto-N-methylbenzamide)-3-((E) -2-pyridin-2-vinyl)-1-(tetrahydropyroan -2yl)-1H-indazole;(E)-N-methyl-2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)benzamide
• CAS NO: 885126-35-2
• Molecular Formula: C27H26N4O2S
• Molecular Weight: 470.59
• Mol File: 885126-35-2.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 714.2 °C at 760 mmHg
• Flash Point: 385.8 °C
• Appearance: /
• Density: 1.28
• CAS DataBase Reference: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide(885126-35-2)
• EPA Substance Registry System: N-Methyl-2-[[3-[(1E)-2-(2-pyridinyl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio]benzamide(885126-35-2)

Safety Data

• Hazardous Substances Data: 885126-35-2(Hazardous Substances Data)

Usage

Uses

Axitinib Tetrahydro-2H-pyran is an intermediate in the synthesis of Axitinib (A794650). The Tetrahydro-2H-pyran moiety acts as a protecting group.

Upstream product

• 100-69-6 2-vinylpyridine 
• 885126-36-3 N-1 THP-protected 2-(3-iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide 
• 150187-67-0 6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 
• 110-87-2 3,4-dihydro-2H-pyran 
• 886230-74-6 3-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole 
• 319460-85-0 axitinib 
• 885521-84-6 3,6-dibromo-1H-indazole 
• 79762-54-2 6-bromo-1H-indazole 
• 20054-45-9 N-methyl-2-sulfanylbenzamide 
• 70315-70-7 3-iodo-6-nitro-1H-indazole 
• 2527-58-4 2,2'-dithiobis(N-methylbenzamide) 
• 19602-82-5 2,2'-dithiodibenzoic acid dichloride 
• 119-80-2 2,2'-dithiobenzoic acid 
• 7597-18-4 6-nitroindazole 

Relevant articles and documents

Prodrug compound and application thereof in treatment of cancer

The present invention provides a compound indicated by a formula (I), pharmaceutically acceptable salts or esters thereof, a pharmaceutical composition of the compound, and the use of the compound andthe pharmaceutical composition in inhibition or regulation of tyrosine kinase activity, and treatment of tyrosine kinase mediated disease symptoms or disorders including cancer.

A process for the preparation of intermediates axi for Nepal the preparation and application of axi for Nepal

The invention relates to a method for preparing an intermediate of axitinib and application of the intermediate in preparation of axitinib. The preparation method for the intermediate of axitinib 3-iodine-6-nitro-1-(teralin-2H-pyran-2-base)-1H-indazole comprises the following steps that 6-nitroindazole and 3,4-dihydro-2H-pyran react under the action of catalyst so as to protect perssad tetralin-2H-pyran-2-base at N-H site, and the key intermediate with high yield is obtained through iodination at site 3. The application of the intermediate in preparation of axitinib is as follows: Heck coupled reaction is carried out on the intermediate and 2-vinyl pyridine, then nitro reduction and diazo-reaction for iodination are sequentially carried out, finally, the axitinib is obtained after docking of 2-sulfydryl-N-methyl benzamide and deprotection. The related main initial raw materials are easy to purchase in markets, and the method has high yield and high molecule economic efficiency, is efficient and environment-friendly, and is suitable for industrial mass production.

Effective Laboratory-Scale Preparation of Axitinib by Two CuI-Catalyzed Coupling Reactions

The discovery and development of an efficient synthesis route to axinitib is reported. The first-generation route researched by Pfizer implemented two Pd-catalyzed coupling reactions as key steps. In this work, the development of Heck-type and C-S coupling reactions catalyzed by CuI is briefly described, using an economial and practical protocol. Aspects of this route, such as selecting optimal ligands, solvent, and other conditions, are discussed in detail. The scale-up experiment was carried out to provide more than 300 g of active pharmaceutical ingredients of axitinib in Form XLI with 99.9% purity in 39% yield. In short, we provide a new choice of synthesis route to axitinib, through two copper-catalyzed coupling reactions with good yield.