Tenatoprazole

Base Information

• Chemical Name: Tenatoprazole
• CAS No.: 113712-98-4
• Molecular Formula: C16H18N4O3S
• Molecular Weight: 346.41
• European Community (EC) Number: 601-277-6
• UNII: RE0689TX2K
• DSSTox Substance ID: DTXSID1046687
• Nikkaji Number: J1.037.122H
• Wikipedia: Tenatoprazole
• Wikidata: Q4822824
• NCI Thesaurus Code: C90934
• ChEMBL ID: CHEMBL1475252
• Mol file: 113712-98-4.mol

Synonyms:5-methoxy-2-(((4-methoxy-3,5-dimethylpyrid-2-yl)methyl)sulfinyl)-1H-imidazo(4,5-b)pyridine;5-methyl-2((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl-imidazo(4,5-b)pyridine;Tenatoprazole;TU 199;TU-199;TU199

Chemical Property of Tenatoprazole

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 5.8E-14mmHg at 25°C
• Melting Point: 178-180°C
• Refractive Index: 1.673
• Boiling Point: 591.5 °C at 760 mmHg
• PKA: 4.61±0.40(Predicted)
• Flash Point: 311.5 °C
• PSA: 109.20000
• Density: 1.41 g/cm³
• LogP: 3.16040
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 346.10996162
• Heavy Atom Count: 24
• Complexity: 455

Purity/Quality:

99.0%Min ^*data from raw suppliers

Tenatoprazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=CC(=N3)OC
• Description: Tenatoprazole is a proton pump inhibitor, blocking hog gastric H+/K+-ATPase activity with an IC50 value of 6.2 μM. It is orally bioavailable, blocking induced gastric acid secretion and ulcer formation in rats and humans. Tenatoprazole has a prolonged plasma half-life resulting in persistent effectiveness after withdrawal.
• Uses: A proton pump inhibitor for reduction and/or prevention of gastrointestinal disorders A proton pump inhibitor for reduction and/or prevention of gastrointestinal disorders.

Technology Process of Tenatoprazole

There total 3 articles about Tenatoprazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.4%

5-methoxy-2-[(4-nitro-3,5-dimethyl-2-pyridinyl)methylsulfinyl]imidazo[4,5-b]pyridine + sodium methylate (124-41-4) → tenatoprazole (113712-98-4)

Guidance literature:

In methanol; at -5 ℃; for 18h;

DOI:10.1080/00397910701797913

Reference yield: 74.0%

5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine (113713-24-9) → tenatoprazole (113712-98-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at -15 - -10 ℃; Large scale reaction;

DOI:10.1021/op800173u

Reference yield:

5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine (113713-24-9) → 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfonyl)-1H-imidazo[4,5-b]pyridine + tenatoprazole (113712-98-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 5 ℃; for 0.0166667h; Product distribution / selectivity;

upstream raw materials:

sodium methylate

5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine

Downstream raw materials:

5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-1H-imidazo[4,5-b]pyridine

2-tosylethyl 2-{4-[5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1H-imidazo[4,5-b]pyridine-1-ylsulfonyl]-phenoxy}-acetate

2-tosylethyl 2-{4-[5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-3H-imidazo[4,5-b]pyridine-3-ylsulfonyl]-phenoxy}-acetate

Refernces

• 1、 Reddy, Ganta Madhusudhan,Prasada Raju,Babu, J. Moses,Praveen,Khunt, Mayur,Mukkanti,Pratap Reddy, Padi. "Synthesis and characterization of metabolites and potential impurities of the antiulcerative drug tenatoprazole". . p. 1725 - 1736. Retrieved 2008.
• 2、 Sripathi, Somaiah,Bojja, Ramachandra Reddy,Karnati, Venugopal Reddy,Prasada Raju,Khunt, Mayur D.. "An improved synthesis of antiulcerative drug: Tenatoprazole". . p. 804 - 806. Retrieved 2009.
• 3、 -. "Continuous Flow Process For The Preparation Of Sulphoxide Compounds". Page/Page column 4. . Retrieved 2012/08/27.