113713-24-9

Basic information

• Product Name: 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE
• Synonyms: 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE;5-Methoxy-2-(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio)-3H-imidazo[4,5-b]pyridine;5-Methoxy-2-(((4-Methoxy-3,5-diMethylpyridin-2-yl)Methyl)thio)-1H-benzo[d]iMidazole;5-Methoxy-2-(((4-Methoxy-3,5-diMethylpyridin-2-yl)Methyl)thio)-1H-iMidazo[4,5-b]pyridine;5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]thio]-3H-Imidazo[4,5-b]pyridine;5-METHOXY-2[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)-2-METHYL]THIO]-1H-BENZIMIDAZOLE
• CAS NO: 113713-24-9
• Molecular Formula: C₁₆H₁₈N₄O₂S
• Molecular Weight: 330.4
• Mol File: 113713-24-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 152-154 °C(Solv: dichloromethane (75-09-2))
• Boiling Point: 530.736 °C at 760 mmHg
• Flash Point: 274.78 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.653
• PKA: 5.83±0.40(Predicted)
• CAS DataBase Reference: 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE(113713-24-9)
• EPA Substance Registry System: 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE(113713-24-9)

Safety Data

• Hazardous Substances Data: 113713-24-9(Hazardous Substances Data)

Usage

General Description

5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE is a chemical compound with a complex structure containing a 5-methoxy group, a 2-imidazo[4,5b]pyridine ring, and a 4-methoxy-3,5-dimethyl-2-pyridinylmethylthio group. 5-METHOXY-2-[[(4-METHOXY-3,5-DIMETHYL-2-PYRIDINYL)METHYL]THIO]-1H-IMIDAZO[4,5B]PYRIDINE belongs to the class of imidazopyridines, which are often used in medicinal chemistry as potential drug candidates for a variety of therapeutic applications. The presence of the methoxy and methyl groups in its structure suggests that it may have pharmacological properties, and it could potentially be used in the development of new drugs targeting various biological pathways. However, further research would be needed to assess its specific biological activity and potential applications.

InChI:InChI=1/C16H18N4O2S/c1-9-7-17-12(10(2)14(9)22-4)8-23-16-18-11-5-6-13(21-3)19-15(11)20-16/h5-7H,8H2,1-4H3,(H,18,19,20)

Upstream product

• 113712-98-4 tenatoprazole 
• 153476-67-6 5-methoxy-2-[(4-nitro-3,5-dimethyl-2-pyridinyl)methylthio]imidazo[4,5-b]pyridine 
• 124-41-4 sodium methylate 
• 86604-75-3 2-(chloromethyl)-4-methoxy-3,5-dimethylpyridine hydrochloride 

Downstream Products

• 113712-98-4 tenatoprazole 
• 119141-88-7 (S)-6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]-sulfinyl]-1H-benzimidazole 
• 119141-89-8 (R)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1H-benzoimidazole 

Relevant articles and documents

Regioselective hydroxylation pathway of tenatoprazole to produce human metabolites by Bacillus megaterium CYP102A1

Tenatoprazole, a proton pump inhibitor drug candidate, is developed as an acid inhibitor to treat gastric acid hypersecretion disorders, such as gastric ulcer and reflux esophagitis. Tenatoprazole is known to be metabolized to three major metabolites—tenatoprazole sulfone, 5’-hydroxylated metabolite, and tenatoprazole sulfide—in human livers mainly by CYP2C19 and CYP3A4. In this study, an enzymatic strategy for the production of human metabolites of tenatoprazole was developed using bacterial P450 enzymes. A set of CYP102A1 mutants catalyzed the regioselective hydroxylation reactions of tenatoprazole. The major product of tenatoprazole by CYP102A1 is 5’-OH tenatoprazole, a major human metabolite produced by human CYP2C19 and CYP3A4. As another major metabolite of tenatoprazole, tenatoprazole sulfide is formed via a non-enzymatic conversion without a P450 system. In addition, 5’-OH tenatoprazole sulfide was found as a minor metabolite, which can be formed via a 5’-hydroxylation reaction of tenatoprazole sulfide by CYP102A1 and/or a non-enzymatic reduction of 5’-OH tenatoprazole to a sulfide form. Chemical synthesis of the 5’-OH tenatoprazole is not currently possible. In conclusion, an enzymatic synthesis of 5’-OH tenatoprazole, a major human metabolite of tenatoprazole, was developed by using mutants of CYP102A1 from Bacillus megaterium as a biocatalyst and tenatoprazole as a substrate.

An improved synthesis of antiulcerative drug: Tenatoprazole

An efficient, cost-effective and multikilogram-scale process for the synthesis of tenatoprazole 1, an antiulcerative drug, is described. The key steps in this synthesis involve the coupling of 2-mercapto-5-methoxyimidazo[4,5- b]pyridine 2 with 2-chloromethyl-4-methoxy-3,5-dimethyl pyridine hydrochloride 3 to yield 4 and its subsequent oxidation with m-CPBA to produce sulfoxide 1. The process has been scaled up for the multikilogram-scale of compound 1 with an overall yield of 72%. The new process requires no purification process and affords the target compound 1 with 99.8% purity by HPLC.

Improved synthetic approach to tenatoprazole

An improved synthetic approach to tenatoprazole 1 is described. It started from 2,3,5-trimethyl-4-nitropyridine-N-oxide 2 with acetic anhydride via rearrangement and hydrolysis to give 3, Chlorination with SOCl2 yielded 2-chloromethyl-3,5-dimethyl-4-nitropyridine hydrochloride 4, then 4 condensed with 2-mercapto-5-methoxy imidazole [4,5-b]pyridine 5 to give 5-methoxy-2-[(4-nitro-3,5-dimethyl-2-pyridinyl)methylthio]imidazole[4,5-b] pyridine 6. At last the title compound 1 was produced by two methods: 6 was oxidized with MCPBA and then methoxylated with CH3ONa to give 1 and 6 was first methoxylated with CH3ONa and then oxidized with MCPBA to give 1. The overall yield is around 26% for both five-step syntheses. Copyright Taylor & Francis Group, LLC.