20054-45-9

Basic information

• Product Name: N-methyl-2-sulfanylbenzamide
• Synonyms: N-methyl-2-sulfanylbenzamide;BenzaMide, 2-Mercapto-N-Methyl-;2- Mercapto-N-MethyllbenzaMide;2-MERCAPTO-N-METHYL BENZAMIDE(RE-EXPORTWIDE B/E.NO:2513786 DT 08.09.2015)
• CAS NO: 20054-45-9
• Molecular Formula: C8H9NOS
• Molecular Weight: 167.231
• EINECS: 1592732-453-0
• Product Categories: Intermediate
• Mol File: 20054-45-9.mol

Chemical Properties

• Melting Point: 94-96 °C
• Boiling Point: 326.2 °C at 760 mmHg
• Flash Point: 151.1 °C
• Appearance: /
• Density: 1.174
• Storage Temp.: 2-8°C
• PKA: 5.89±0.43(Predicted)
• CAS DataBase Reference: N-methyl-2-sulfanylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-methyl-2-sulfanylbenzamide(20054-45-9)
• EPA Substance Registry System: N-methyl-2-sulfanylbenzamide(20054-45-9)

Safety Data

• Hazardous Substances Data: 20054-45-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-methyl-2-sulfanylbenzamide is used as an intermediate in the synthesis of axitinib, a tyrosine kinase inhibitor, for cancer therapy. Axitinib targets various cancer-related pathways, such as VEGFR, PDGFR, and c-Kit, thereby inhibiting angiogenesis and tumor growth. It is particularly effective in treating advanced renal cell carcinoma and other solid tumors.
Used in Cancer Therapy:
N-methyl-2-sulfanylbenzamide is used as a key component in the development of axitinib, which is employed as an anticancer agent. Axitinib has demonstrated efficacy in treating various types of cancer, including renal cell carcinoma, hepatocellular carcinoma, and non-small cell lung cancer. Its tyrosine kinase inhibitory properties contribute to its ability to disrupt cancer cell signaling and proliferation, making it a valuable tool in the fight against cancer.

Upstream product

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Downstream Products

• 343869-24-9 2-(N-methylcarbamoyl)phenyl 2-methylphenyl sulfide 
• 343869-28-3 2-(N-methylcarbamoyl)phenyl 4-chlorophenyl sulfide 
• 343869-32-9 2-(N-methylcarbamoyl)phenyl 4-acetylphenyl sulfide 
• 343869-33-0 2-(N-methylcarbamoyl)phenyl 4-carboxy3henyl sulfide 
• 127905-49-1 2-(N-methylcarbamoyl)phenyl 2-methoxyphenyl sulfide 
• 135781-45-2 2-<2-(N-methylcarbamoyl)phenylthio>benzoic acid 
• 343869-27-2 2-(N-methylcarbamoyl)phenyl 4-methylphenyl sulfide 
• 343869-25-0 2-(N-methylcarbamoyl)phenyl 2-chlorophenyl sulfide 
• 127905-51-5 2-(N-methylcarbamoyl)phenyl 4-methoxyphenyl sulfide 
• 252731-18-3 2-(N-methylcarbamoyl)phenyl 2-nitrophenyl sulfide 
• 100695-82-7 2-(N-methylcarbamoyl)phenyl 2-(methoxycarbonyl)phenyl sulfide 
• 343869-30-7 2-(N-methylcarbamoyl)phenyl 4-(methoxycarbonyl)phenyl sulfide 
• 343869-26-1 2-(N-methylcarbamoyl)phenyl 2-acetylphenyl sulfide 
• 1144043-02-6 C₂₇H₂₅N₃O₄S 

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.

Axitinib intermediate compound and preparation method thereof

The invention belongs to the field of pharmaceutical chemicals, and particularly relates to an axitinib intermediate compound and a preparation method thereof. The present invention provides a novel axitinib intermediate compound S-(2-(methylcarbamoyl) phenyl) dimethylthioformate, the invention also provides a preparation method thereof. The method comprises the following steps: dissolving 2-hydroxy-N-methylbenzamide in an organic solvent, and adding dimethylaminothioformyl chloride and a catalyst to obtain the S-(2-(methylcarbamoyl) phenyl) dimethylthioformate. The new intermediate compound can be used for preparing the axitinib important intermediate 2-sulfydryl-N-methylbenzamide, and the synthesis method provided by the invention is short in route, simple to operate and high in yield and purity of the obtained 2-sulfydryl-N-methylbenzamide, and is suitable for industrial production.

Preparation method of axitinib intermediate

The present invention belongs to the field of medicine synthesis, and particularly relates to a preparation methodof an axitinib intermediate 2-sulfydryl-N-methylbenzamide, the method comprises the following steps: the intermediate compound S-(2-(methylcarbamoyl) phenyl) dimethylthioformate is synthesized by taking 2-hydroxy-N-methylbenzamide as a raw material under the action of a catalyst, and the new intermediate is further synthesized into the 2-sulfydryl-N-methylbenzamide under the action of alkali. The synthesis method provided by the invention is short in route and simple to operate, and the obtained 2-sulfydryl-N-methylbenzamide is high in yield, high in purity and more suitable for industrial production.

ALKYNYL INDAZOLE DERIVATIVE AND USE THEREOF

The main object of the present invention is to provide a novel compound which has a VEGF receptor tyrosine kinase inhibitory activity and is useful as an active ingredient for the treatment of diseases accompanying angiogenesis or edema, for example, age-related macular degeneration or the like. The present invention includes, for example, an alkynyl indazole derivative represented by the following general formula (I), a pharmaceutical acceptable salt thereof, and a medicine containing thereof.

NOVEL ULK1 INHIBITORS AND METHODS USING SAME

In certain aspects, the invention provides a method for treating a disease or condition in a subject, the method comprising co-administering to a subject in need thereof a therapeutically effective amount of at least one ULK1-inhibiting pyrimidine, and a therapeutically effective amount of an mTOR inhibitor.

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.

An umpolung sulfoxide reagent for use as a functionalized benzyl carbanion equivalent

N-Methyl ortho-carbamoylaryl benzyl sulfoxides can be used as synthetic equivalents for α-hydroxy, α-chloro, and α-acetammido benzyl carbanions by means of a two-step sequence involving highly diastereoselective α-C-alkylation with alkyl halides followed by displacement of the sulfinyl residue (which can be recovered and recycled) by a hydroxyl, a chlorine or an acetamido, respectively, under non-oxidative Pummerer conditions. The scope and limits of the method, including a stereoselective version of the reaction, as well as the mechanism of the process are discussed in detail.

Design, syntheses, and characterization of dioxo-molybdenum(vi) complexes with thiolate ligands: Effects of intraligand NH...S hydrogen bonding

Presence of the hydrogen bonding near a metal center can influence the properties of the complex. Here, we describe changes in redox and spectral properties in discrete dioxo-molybdenum centers coordinated by a single thiolato ligand that can support an intra-ligand hydrogen bond. We have utilized thiophenolato ligands that can harbor hydrogen bonding between the thiophenolato sulfur with an amide functionality creating either a five- or a six-membered ring. Methylation of the amide functionality removes the NH...S hydrogen bonding thus providing a basis for understanding the effect of hydrogen bonding. These thiophenolato ligands have been used in synthesizing dioxo-MoVI complexes of type Tp*MoO2(S-o-RC6H4), where R = CONHMe (11), CONMe2 (12), NHCOMe (13), and N(Me)COMe (14). The complexes have been characterized by NMR, infrared, and UV-visible spectroscopy. Spectroscopic data clearly indicate the presence of hydrogen bonding in both 11 and 13, and stronger in 13, where hydrogen bonding stabilizes a five-membered ring. All complexes exhibit a MoVI/MoV redox couple and redox potentials are modulated by the nature of H-bonding. Compound 14 with the electron-releasing N(Me)COMe group has the highest reduction potential and is more difficult to reduce. The Royal Society of Chemistry.

Novel alternative for the N-S bond formation and its application to the synthesis of benzisothiazol-3-ones

(Chemical Equation Presented) The synthesis of a series of benzisothiazolone derivatives starting from the readily available methyl thiosalicylate is presented. The key cyclization step features the formation of a N-acylnitrenium ion, generated by the hypervalent iodine reagent PIFA, and its succeeding intramolecular trapping by the thiole moiety leading to the construction of the title compounds by formation of a new N-S bond.

METHODS FOR PREPARING INDAZOLE COMPOUNDS

The invention relates to methods for preparing indalzole compounds having formula (I) or pharmaceutically acceptable salts or solvates thereof. Compounds of the formula (I) are useful as anti-angiogenesis agents and as agents for modulating and/or inhibiting the activity of protein kinases, thus providing treatments for cancer or other diseases associated with cellular proliferation mediated by protein kinases.