113713-60-3

Basic information

• Product Name: 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine
• Synonyms: 2-Mercapto-5-methoxy-3H-imidazo[4,5-b]pyridine;5-Methoxy-3H-imidazo[4,5-b]pyridine-2-thiol;1,3-dihydro-5-methoxy-;2H-Imidazo[4,5-b] pyridine-2-thione;2-Mercapto-5-methoxy-3H-imidazole-[4,5-b]pyridine ,98%;1,3-Dihydro-5-Methoxy-2H-Imidazo(4,5-b)Pyridine-2-Thione;2H-Imidazo[4,5-b]pyridine-2-thione, 1,3-dihydro-5-methoxy-;5-MethoxyiMidazo-[4,5-b]pyridine-2-thiol (InterMediate of TTZ) 2-Mercapto-5-MethoxyiMidazole[4,5-b]pyridine
• CAS NO: 113713-60-3
• Molecular Formula: C₇H₇N₃OS
• Molecular Weight: 181.21
• EINECS: 1312995-182-4
• Product Categories: (intermediate of tenatoprazole);Heterocycle-Pyridine series;Imidazoles
• Mol File: 113713-60-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 238-241°C
• Boiling Point: 314.532 °C at 760 mmHg
• Flash Point: 144.024 °C
• Appearance: /
• Density: 1.47 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.705
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 7.39±0.40(Predicted)
• CAS DataBase Reference: 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine(113713-60-3)
• EPA Substance Registry System: 2-Mercapto-5-methoxyimidazole[4,5-b]pyridine(113713-60-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 113713-60-3(Hazardous Substances Data)

Usage

Chemical Properties

White to gray solid

InChI:InChI=1/C7H7N3OS/c1-11-5-3-2-4-6(9-5)10-7(12)8-4/h2-3H,1H3,(H2,8,9,10,12)

Upstream product

• 73896-36-3 6-methoxy-3-nitropyridin-2-amine 
• 75-15-0 carbon disulfide 
• 28020-38-4 2,3-diamino-6-methoxypyridine 

Relevant articles and documents

Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.

Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.