1H-Imidazo[4,5-b]pyridine

Base Information

• Chemical Name: 1H-Imidazo[4,5-b]pyridine
• CAS No.: 273-21-2
• Deprecated CAS: 39514-47-1
• Molecular Formula: C6H5N3
• Molecular Weight: 119.126
• Hs Code.: 2933990090
• European Community (EC) Number: 205-987-3
• NSC Number: 403091
• DSSTox Substance ID: DTXSID9075375
• Nikkaji Number: J193.696D
• Wikidata: Q27126982
• Metabolomics Workbench ID: 60890
• ChEMBL ID: CHEMBL4476663
• Mol file: 273-21-2.mol

Synonyms:1-deazapurine;1H-imidazo(4,5-b)pyridine

Chemical Property of 1H-Imidazo[4,5-b]pyridine

Chemical Property:

• Appearance/Colour: yellow to light brown powder
• Vapor Pressure: 0.114mmHg at 25°C
• Melting Point: 148-151 °C(lit.)
• Refractive Index: 1.728
• Boiling Point: 1.348 g/cm³
• PKA: 8.46±0.20(Predicted)
• Flash Point: 395.3 °C at 760 mmHg
• PSA: 41.57000
• Density: 1.38g/cm3
• LogP: 0.95790
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Soluble in dimethylformamide.
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.048347172
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

97% ^*data from raw suppliers

4-Azabenzimidazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(N=C1)N=CN2
• Uses: 4-Azabenzimidazole is used in the preparation of imidazo[4,5-b]pyridine 4-oxide. It is also used as a reagent to prepare benzoylmethyl-substituted azoles which are inhibitors of nitric oxide synthase with antioxidant properties.

Technology Process of 1H-Imidazo[4,5-b]pyridine

There total 33 articles about 1H-Imidazo[4,5-b]pyridine 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: 99.0%

2,3-Diaminopyridine (452-58-4) + orthoformic acid triethyl ester (122-51-0) → 3H-imidazo[4,5-b]pyridine (273-21-2)

Guidance literature:

2,3-Diaminopyridine; orthoformic acid triethyl ester; at 145 ℃; for 3h;

With formic acid; at 110 ℃; for 2h;

DOI:10.1002/chem.201102279

Reference yield: 99.0%

2,3-Diaminopyridine (452-58-4) + formic acid (64-18-6) → 3H-imidazo[4,5-b]pyridine (273-21-2)

Guidance literature:

2,3-Diaminopyridine; With orthoformic acid triethyl ester; at 145 ℃; for 3h;

formic acid; at 110 ℃; for 2h;

In methanol; at 20 ℃;

DOI:10.1002/cbic.201800665

Reference yield: 90.0%

6-bromo-3H-imidazo[4,5-b]pyridine (28279-49-4) → 3H-imidazo[4,5-b]pyridine (273-21-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201600166

upstream raw materials:

2,3-Diaminopyridine

formic acid

6-chloro-1⁽³⁾H-imidazo[4,5-b]pyridine

2-chloro-imidazo[4,5-b]pyridine

Downstream raw materials:

1-(Phenylmethyl)-1H-imidazo<4,5-b>pyridine

4-(Phenylmethyl)-4H-imidazo<4,5-b>pyridine

3-(Phenylmethyl)-3H-imidazo<4,5-b>pyridine

1-ethyl-1H-imidazo[4,5-b]pyridine

Refernces

Optimization of the heterocyclic core of the quinazolinone-derived CXCR3 antagonists

10.1016/j.bmcl.2007.11.060

The study focuses on the optimization of the heterocyclic core of quinazolinone-derived CXCR3 antagonists, which are compounds that block the CXCR3 receptor, a chemokine receptor involved in immune cell trafficking and implicated in various inflammatory and autoimmune diseases. The researchers synthesized a series of six-six and six-five fused heterocyclic CXCR3 antagonists and evaluated their activities in displacement assays and cell migration assays. They also studied the pharmacokinetic properties of several top-performing compounds. The aim was to discover compounds with increased potency and improved pharmacokinetic properties that could serve as tools to study the role of the CXCR3 receptor in vivo. The chemicals used in the study included various heterocyclic compounds such as quinoline, 1,8-naphthyridine, quinoxaline, benzoimidazole, imidazopyridine, imidazopyrimidine, and pyrozolopyridine derivatives. These chemicals were designed to replace the 8-aza-quinazolinone core of the existing CXCR3 antagonist AMG 487, with the goal of improving binding affinity to the CXCR3 receptor and potentially enhancing therapeutic efficacy in treating diseases like psoriasis, multiple sclerosis, inflammatory bowel disease, and rheumatoid arthritis.

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