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

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

Uses

Used in Pharmaceutical Industry:
1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYLis used as a building block in chemical synthesis for the development of antihypertensive agents. Its imidazo[4,5-b]pyridine scaffold allows for various positional substitutions, leading to the creation of orally active and long-duration medications for the treatment of high blood pressure.
Used in Organic Synthesis:
1H-IMIDAZO[4,5-B]PYRIDINE, 2-ETHYL-5,7-DIMETHYLis used as a compound in organic synthesis, contributing to the development of new chemical products and innovations in various industries.

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 
• 89856-44-0 2-amino-5-bromo-4,6-dimethylpyridine 
• 7144-20-9 2-Amino-4,6-dimethylnicotinamide 
• 123-54-6 acetylacetone 
• 5407-87-4 2-Amino-4,6-dimethylpyridine 
• 89791-76-4 2-amino-3-nitro-4,6-dimethyl-5-bromo-pyridine 
• 39739-45-2 methylpropioimidate hydrochloride 
• 540-61-4 2-aminoacetonitrile 

Downstream Products

• 700376-55-2 2-[4-[(5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]phenyl]-3-pyridinecarbonitrile 
• 700376-31-4 4-[4-[(5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]phenyl]-3-[2-(triphenylmethyl)-2H-tetrazol-5-yl]quinoline 
• 700376-35-8 4-[4-[(5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]phenyl]-1-methyl-3-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-2(1H)quinolinone 
• 155380-12-4 [4-(2-ethyl-5,7-dimethyl-imidazo[4,5-b]pyridin-3-ylmethyl)-phenyl]-acetic acid methyl ester 
• 1197880-36-6 2-ethyl-3-(4-methoxy-benzyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine 
• 163520-13-6 2-ethyl-3-(4-iodo-benzyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine 
• 1197879-16-5 (E)-2-ethyl-3-(4-(3-(4-isopropylpiperazin-1-yl)prop-1-en-1-yl)benzyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine 
• 1197880-09-3 (E)-methyl 3-(4-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)phenyl)acrylate 
• 137420-96-3 3-[3-chloro-4-((1-carbomethoxy-1-phenyl)methoxy)phenyl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine 
• 163339-47-7 3-[4-(1-carbomethoxy-1-phenylmethoxy)-3-chloro-5-(prop-2-ene-1-yl)phenylmethyl]-5,7-dimethyl-2-ethyl-3H-imidazo-[4,5-b]pyridine 
• 137421-60-4 3-[(4-nitrophenyl)methyl]-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine 
• 153465-66-8 2-{6-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl]quinolin-2-yl}benzoic acid 
• 150094-70-5 4'-[[5,7-Dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridin-3yl]methyl][1,1'-biphenyl-2-yl]carboxylic acid methyl ester 

Relevant articles and documents

BIARYLMETHYL HETEROCYCLES

The present invention provides compounds of Formula (I): wherein all variables are as defined in the specification, and compositions comprising any of such novel compounds. These compounds are biased agonists, or β-Arrestin agonists of the angiotensin II receptor, which may be used as medicaments.

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.

2,6,8-Trisubstituted 1-deazapurines as adenosine receptor antagonists

In this study we developed a refined pharmacophore model for antagonists of the human adenosine A1 receptor, based on features of known pyrimidine and purine derivatives. The adoption of these updated criteria assisted us in synthesizing a series of 1-deazapurines with consistently high affinity as inverse agonists for the adenosine A1 receptor. These 1-deazapurines (otherwise known as 3H-imidazo[4,5-b]pyridines) were substituted at their 2- and 6-positions, yielding a series with five of the derivatives displaying Ki values in the subnanomolar range. The most potent of these, compound 10 (LUF 5978), displayed an affinity of 0.55 nM at the human adenosine A1 receptor with > 300-fold and 45-fold selectivity toward A2A and A3 receptors, respectively. Compound 14 (LUF 5981, Ki = 0.90 nM) appeared to have the best overall selectivity with respect to adenosine A2A (> 200-fold) and A 3 (700-fold) receptors.

3N-Methylbiphenylsulfonylurea and -carbamate substituted imidazo[4,5-b]pyridines. Potent antagonists of the ANG II AT1 receptors

The synthesis and the SAR study of imidazo[4,5-b]pyridine biphenyl sulfonylureas and -carbamates as highly potent AT1-seIective ANG II receptor antagonists are described. Several members of this new class of antagonists efficiently inhibited the ANG II-induced presser response in pithed rats after iv and intraduodenal (id) administration.

Polymorphic forms of an angiotensin II antagonist

Polymorphic forms of the angiotensin II receptor antagonist, 3-[2''-(N-benzoyl)sulfonamidobiphenyl-4-yl]methyl-5,7-dimethyl-2-ethyl-3H-imidazo[4,5-b]pyridine and a method for the preparation of these crystal forms.

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.

New approach to the imidazolutidine moiety of MK-996

A highly effective, regio-selective synthesis of imidazolutidine (1) is described starting from readily available malonamamidine hydrochloride and 2,4-pentanedione.

IMIDAZOPYRIDINE DERIVATIVES AS ANGIOTENSIN II ANTAGONISTS

The present invention relates to new imidazopyridine derivatives of formula I STR1 wherein: one of A, B, C and D is N and the other are CR, wherein each R independently represents hydrogen, C 1-4 alkyl, COOH or halogen; R 1 represents C 1-4 alkyl or C 3-7 cycloalkyl; Ar 1 represents phenyl or pyridyl which can be optionally substituted; V represents C 1-4 alkyl, C 3-7 cycloalkyl, aryl, aryl-(C 1-4)alkyl or a 5-or 6-membered aromatic heterocycle; the group X-Y represents C=C or CH--CR 3 ; R 3 represents hydrogen, C 1-4 alkyl or aryl-(C 1-4)alkyl; Z represents among others--CO 2 R 4,--tetrazol-5-yl,--CONHSO 2 R 4,--CONR 4 R 5,--CH 2 NHSO 2 R 4 ; R 4 and R 5 independently represent hydrogen, C 1-4 alkyl, aryl, aryl-(C 1-4) alkyl or perfluoro-(C 1-4) alkyl; W represents hydrogen, cyano, C 1-4 alkyl, C 1-4 haloalkyl, C 3-7 cycloalkyl, aryl, aryl-(C 1-4)alkyl, C 1-4 alkylsulfonyl, C 1-4 alkylsulfinyl, C 1-4 alkylthio, C 1-4 alkoxy, C 1-4 alkylcarbonyl, halogen, hydroxymethyl or C 1-4 alkoxymethyl, or W can have any of the meanings disclosed for Z. These compounds are angiotensin II antagonists.

Substituted benzoxazole, benzthiazole, and benzimidazole derivatives as angiotensin II antagonists

The invention concerns pharmaceutically useful compounds of the formula I, in which Q, X, Z and Ra have the various meanings defined herein, and their non-toxic salts, and pharmaceutical compositions containing them for treating conditions as hypertension and congestive heart failure.

Process for preparing imidazopyridine derivatives

A new process for preparing imidazopyridines of the general formula: STR1 wherein R1 is an alkyl, cycloalkyl, aryl or aralkyl group or is a heterocyclic radical, R2 and R4 are identical or different and are hydrogen, a hyd