103577-40-8

Basic information

• Product Name: 2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole
• Synonyms: 2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-yl]methylthio]-1H-benzoimidazole;2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinylmethylthio]-1H-benzoimidazole;2-[3-Methyl-4-(2,2,2;Lansoprazole Related Compound B (25 mg) (2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-yl]methyl]sulfanyl]-1H-benzimidazole);2-{[3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]Methyl}-1H-1,3-benzodiazole-1-thiol;2-(((3-Methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl)Methyl)thio)-1H-benzo[d]iMidazole;Lansoprazole related substance C;2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]Methyl]thio]-
• CAS NO: 103577-40-8
• Molecular Formula: C₁₆H₁₄F₃N₃OS
• Molecular Weight: 353.36
• EINECS: 1533716-785-6
• Product Categories: Imidazol&Benzimidazole;(intermediate of lansoprazole);Heterocyclic Compounds;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Lansoprazole
• Mol File: 103577-40-8.mol
• Article Data: 29

Chemical Properties

• Melting Point: 149-150°C
• Boiling Point: 494.9 °C at 760 mmHg
• Flash Point: 253.1 °C
• Appearance: /Crystalline Powder
• Density: 1.41
• Vapor Pressure: 6.2E-10mmHg at 25°C
• Refractive Index: 1.615
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 10.60±0.10(Predicted)
• CAS DataBase Reference: 2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole(103577-40-8)
• EPA Substance Registry System: 2-[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methylthio-1H-benzimidazole(103577-40-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 103577-40-8(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 103577-40-8 differently. You can refer to the following data:
1. A metabolite of Lansoprazole, as gastric pump inhibitor
2. Lansoprazole Sulfide (Lansoprazole EP Impurity C; USP Impurity B) is a metabolite of Lansoprazole, as gastric pump inhibitor.

InChI:InChI=1/C16H14F3N3OS/c1-10-13(20-7-6-14(10)23-9-16(17,18)19)8-24-15-21-11-4-2-3-5-12(11)22-15/h2-7H,8-9H2,1H3,(H,21,22)

Upstream product

• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 
• 134469-07-1 Benzimidazol-2-thiol 
• 103577-45-3 lansoprasole 
• 103577-66-8 2-Hydroxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 
• 75-09-2 dichloromethane 
• 1427321-51-4 2-[[[3-Methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]-methyl]thio]-1H-benzimidazole 2-propanol 
• 103577-61-3 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide 
• 128430-66-0 2-(chloromethyl)-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 

Downstream Products

• 103577-45-3 lansoprasole 
• 131926-99-3 Lansoprazole sulfone 
• 138530-95-7 (S)-lansoprazole 
• 138530-94-6 (R)-lansoprazole 
• 953787-54-7 2-[(3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 

Relevant articles and documents

A practical one pot synthesis of 2-[2-(pridylmethyl)-thio]-1H-benzimidazoles

A combination of Et3N and pTSCl was found to be far superior than pTSCl or benzene sulfonyl chloride alone in convert ing substituted 2-picoline-N-oxides to the corresponding 2-chloromethylpyridines and has been exploited for the synthesis of a variety of 2-[2-(pyridylmethyl)-thio]-1H-benzimidazoles, key intermediates in the manufacture of H+/K+-ATPase inhibitors in a single pot.

Preparation method of thioether

The preparation method comprises the following steps: (a) reacting a halogenated alkyl pyridine derivative or a salt thereof with 2 -mercaptobenzimidazole derivative in a water-soluble organic solvent under basic conditions. (b) The reaction solution obtained in step (a) was subjected to first devitrification step and second devitrification step, and purified. The prepared thioether is low in water content, uniform in water content and high in thioether purity, facilitates control of the water content of a reaction system in a subsequent thioether asymmetric oxidation reaction, and ensures high selectivity and reproducibility of asymmetric oxidation reaction. In addition, the preparation method of the thioether provided by the invention is simple in process and good in repeatability, and is more conducive to large-scale production.

Enhanced Antigiardial Effect of Omeprazole Analog Benzimidazole Compounds

Giardiasis is a diarrheal disease that is highly prevalent in developing countries. Several drugs are available for the treatment of this parasitosis; however, failures in drug therapy are common, and have adverse effects and increased resistance of the parasite to the drug, generating the need to find new alternative treatments. In this study, we synthesized a series of 2-mercaptobenzimidazoles that are derivatives of omeprazole, and the chemical structures were confirmed through mass, 1H NMR, and 13C NMR techniques. The in vitro efficacy compounds against Giardia, as well as its effect on the inhibition of triosephosphate isomerase (TPI) recombinant, were investigated, the inactivation assays were performed with 0.2 mg/mL of the enzyme incubating for 2 h at 37 ?C in TE buffer, pH 7.4 with increasing concentrations of the compounds. Among the target compounds, H-BZM2, O2N-BZM7, and O2N-BZM9 had greater antigiardial activity (IC50: 36, 14, and 17 μM on trophozoites), and inhibited the TPI enzyme (K2: 2.3, 3.2, and 2.8 M?1 s?1) respectively, loading alterations on the secondary structure, global stability, and tertiary structure of the TPI protein. Finally, we demonstrated that it had low toxicity on Caco-2 and HT29 cells. This finding makes it an attractive potential starting point for new antigiardial drugs.

Preparation method for dexlansoprazole

The invention discloses a preparation method for dexlansoprazole, belonging to the field of organic synthesis. The method comprises the following steps: (1) carrying out reaction on 2-hydroxymethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine and thionyl chloride, and compounding 2-chloromethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine; (2) putting 2-chloromethyl-3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine acquired in the step (1) and 2-sulfydryl-1H-benzimidazole into an aqueous liquid, and then adding a phase transfer catalyst and sodium hydroxide, thereby acquiring 2-[[3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine-2-group] methylmercapto]-1H-benzimidazole; (3) taking L-ethyl tartrate as a chiral assistant agent, titanium isopropoxide and diisopropylethylamine as a catalyst and cumyl hydroperoxide as an oxidizing agent and reacting with 2-[[3-methyl-4-(2,2,2-trifluoro ethyoxyl) pyridine-2-group] methylmercapto]-1H-benzimidazole acquired in the step (2) at low temperature, thereby acquiring dexlansoprazole. The preparation method for dexlansoprazole disclosed by the invention is simple and efficient, is capable of obviously shortening the reaction time under the condition of guaranteeing the product yield and is capable of improving the product quality.