133240-06-9

Basic information

• Product Name: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYL-
• Synonyms: 2-ETHYL-5,7-DIMETHYL-3H-IMIDAZO[4,5-B]PYRIDINE;1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYL-;2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-β]pyridine;2-ethyl-5,7-dimethyl-1H-imidazo[4,5-b]pyridine;5,7-DiMethyl-2-ethyliMidazo[4,5-b]pyridine;2-Ethyl-5,7-Dimethyl-3H-Imidazo[4,5-B]Pyridine(WX690021)
• CAS NO: 133240-06-9
• Molecular Formula: C₁₀H₁₃N₃
• Molecular Weight: 175.23
• Product Categories: Aromatics Compounds;Aromatics;Bases & Related Reagents;Heterocycles;Nucleotides;various pyridine derivatives;Pyridine Derivatives
• Mol File: 133240-06-9.mol
• Article Data: 23

Chemical Properties

• Melting Point: 142-146 °C
• Boiling Point: 370.502 °C at 760 mmHg
• Flash Point: 174.175 °C
• Appearance: off-white powder
• Density: 1.14 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol
• PKA: 8.89±0.40(Predicted)
• CAS DataBase Reference: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYL-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYL-(133240-06-9)
• EPA Substance Registry System: 1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYL-(133240-06-9)

Safety Data

• Hazardous Substances Data: 133240-06-9(Hazardous Substances Data)

Usage

Description

2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine is a nonpeptidic angiotensin II receptor antagonist whose imidazo[4,5-b]pyridine scaffold has been used to examine a variety of positional substitutions in the development of orally active, long duration antihypertensive agents.

Chemical Properties

Off-white powder

Uses

Different sources of media describe the Uses of 133240-06-9 differently. You can refer to the following data:
1. 2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine is used as building block in chemical synthesis. Attributes Development Product Contact
2. 2-Ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (cas# 133240-06-9) is a compound useful in organic synthesis.

Synthesis Reference(s)

Tetrahedron Letters, 35, p. 5775, 1994 DOI: 10.1016/S0040-4039(00)78181-0

in vitro

in a previous study, 2-ethyl-5,7-dimethyl-3h-imidazo[4,5-b]pyridine was synthezed by reduction of 2-amino-3-nitropyridine derivatives to the corresponding diaminopyridine which was then condensed with an appropriate carboxylic acid in polyphosphoric acid. in vitro activity study showed that 2-ethyl-5,7-dimethyl-3h-imidazo[4,5-b]pyridine was a nonpeptidic angiotensin ii receptor antagonist whose imidazo[4,5-b]pyridine scaffold had been used to examine plenty of positional substitutions in the development of orally active, long duration antihypertensive agents [1].

references

[1] mantlo, n. b.,chakravarty, p.k.,ondeyka, d.l., et al. potent, orally active imadazo[4,5-b]pyridine-based angiotensin ii receptor antagonists. journal of medicinal chemistry 34(9), 2919-2922 (1991).

InChI:InChI=1/C10H13N3/c1-4-8-12-9-6(2)5-7(3)11-10(9)13-8/h5H,4H2,1-3H3,(H,11,12,13)

Upstream product

• 50850-16-3 2,3-diamino-4,6-dimethylpyridine 
• 802294-64-0 propionic acid 
• 116636-30-7 5,7-dimethyl-1H-imidazo[4,5-b]pyridin-2(3H)-one 
• 123-62-6 propionic acid anhydride 
• 22934-23-2 2-amino-4,6-dimethyl-3-nitropyridine 
• 39739-45-2 methylpropioimidate hydrochloride 
• 123-54-6 acetylacetone 
• 540-61-4 2-aminoacetonitrile 
• 89856-44-0 2-amino-5-bromo-4,6-dimethylpyridine 
• 89791-76-4 2-amino-3-nitro-4,6-dimethyl-5-bromo-pyridine 
• 5407-87-4 2-Amino-4,6-dimethylpyridine 
• 7144-20-9 2-Amino-4,6-dimethylnicotinamide 

Downstream Products

• 137421-56-8 3-[4-tert-butyldimethylsilyloxy-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]-pyridine 
• 137421-58-0 3-[4-((1-carbomethoxy-1-phenyl)methoxy)-3,5-dipropylphenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine 
• 153275-21-9 [4-(2-Ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-2,6-dipropyl-phenoxy]-m-tolyl-acetic acid ethyl ester 

Relevant articles and documents

Magnesium-assisted imidazole formation from unreactive ureas

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Design and synthesis of potent and orally active GPR4 antagonists with modulatory effects on nociception, inflammation, and angiogenesis

GPR4, a G-protein coupled receptor, functions as a proton sensor being activated by extracellular acidic pH and has been implicated in playing a key role in acidosis associated with a variety of inflammatory conditions. An orally active GPR4 antagonist 39c was developed, starting from a high throughput screening hit 1. The compound shows potent cellular activity and is efficacious in animal models of angiogenesis, inflammation and pain.

Innovative approaches to the imidazo[4,5-b]pyridine ring system. Development of an efficient process for industrial-scale production of a key intermediate for potent angiotensin II receptor antagonists

Two syntheses of 2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine (3), an important intermediate for the synthesis of several potent angiotensin II antagonists, have been investigated. The first route involves conversion of 1,1-bis(methylthio)-2-nitroethene (17) to 2-ammo-4,6-dimethyl-3-nitropyridine (6); catalytic hydrogenation of 6 in propionic acid gave 3 in high yield. In the second synthesis, propionitrile is converted to imidate hydrochloride 15·HCl which is neutralised and reacted with aminoacetonitrile in the presence of acetylacetone to give 3 in 55% overall yield. The propionitrile route was scaled up to produce 3 in the pilot plant.