Cas no 1168090-92-3 (Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate)

Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate is a versatile heterocyclic compound featuring a fused imidazopyridine core with a chloro substituent at the 5-position and a methyl ester group at the 6-position. This structure makes it a valuable intermediate in pharmaceutical and agrochemical synthesis, particularly for the development of bioactive molecules. The chloro and ester functionalities enhance reactivity, enabling further derivatization through cross-coupling, nucleophilic substitution, or hydrolysis reactions. Its high purity and stability under standard conditions ensure reliable performance in research and industrial applications. The compound is particularly useful in medicinal chemistry for constructing pharmacophores with potential therapeutic activity.
Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate structure
1168090-92-3 structure
Product Name:Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate
CAS No:1168090-92-3
MF:C9H7ClN2O2
MW:210.617080926895
MDL:MFCD23711382
CID:2094490
PubChem ID:58324565
Update Time:2025-11-02

Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate Chemical and Physical Properties

Names and Identifiers

    • Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate
    • LHXRTDJUZZEEQH-UHFFFAOYSA-N
    • SB17772
    • FCH2335459
    • AK171392
    • 5-Chloroimidazo[1,5-a]pyridine-6-carboxylic acid methyl ester
    • 5-chloro-imidazo[1,5-a]pyridine-6-carboxylic acid methyl ester
    • AKOS025289807
    • AS-51927
    • methyl5-chloroimidazo[1,5-a]pyridine-6-carboxylate
    • 1168090-92-3
    • CS-0048984
    • SCHEMBL1616007
    • Imidazo[1,5-a]pyridine-6-carboxylic acid, 5-chloro-, methyl ester
    • P13922
    • MDL: MFCD23711382
    • Inchi: 1S/C9H7ClN2O2/c1-14-9(13)7-3-2-6-4-11-5-12(6)8(7)10/h2-5H,1H3
    • InChI Key: LHXRTDJUZZEEQH-UHFFFAOYSA-N
    • SMILES: ClC1=C(C(=O)OC)C=CC2=CN=CN21

Computed Properties

  • Exact Mass: 210.0196052g/mol
  • Monoisotopic Mass: 210.0196052g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 2
  • Complexity: 237
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 43.6
  • XLogP3: 2.7

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Additional information on Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate

Research Brief on Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate (CAS: 1168090-92-3): Recent Advances and Applications

Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate (CAS: 1168090-92-3) is a heterocyclic compound that has garnered significant attention in the field of chemical biology and medicinal chemistry due to its versatile applications in drug discovery and development. Recent studies have highlighted its potential as a key intermediate in the synthesis of biologically active molecules, particularly in the development of kinase inhibitors and anti-inflammatory agents. This research brief aims to provide an overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and therapeutic potential.

One of the most notable advancements in the study of Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate is its role in the synthesis of novel kinase inhibitors. Kinases are critical targets in the treatment of various cancers and inflammatory diseases, and the ability to modulate their activity with high specificity is a major focus of current research. Recent publications have demonstrated that derivatives of this compound exhibit potent inhibitory effects against specific kinases, such as JAK2 and BTK, which are implicated in hematologic malignancies and autoimmune disorders. These findings underscore the compound's potential as a scaffold for the development of next-generation therapeutics.

In addition to its applications in kinase inhibition, Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate has also been investigated for its anti-inflammatory properties. A study published in the Journal of Medicinal Chemistry reported that certain analogs of this compound significantly reduced the production of pro-inflammatory cytokines in vitro, suggesting a potential role in the treatment of chronic inflammatory conditions. The mechanism of action appears to involve the modulation of NF-κB signaling, a key pathway in the regulation of immune responses. These results highlight the compound's dual utility in both oncology and immunology.

The synthesis of Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate and its derivatives has also seen significant improvements in recent years. Advances in catalytic methods, such as palladium-catalyzed cross-coupling reactions, have enabled more efficient and scalable production of this compound. These methodological innovations not only enhance the accessibility of the compound for research purposes but also pave the way for its industrial-scale production. Furthermore, the development of greener synthetic routes, including the use of biodegradable solvents and catalysts, aligns with the growing emphasis on sustainable chemistry in pharmaceutical manufacturing.

Despite these promising developments, challenges remain in the optimization of Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate-based therapeutics. Issues such as bioavailability, metabolic stability, and off-target effects need to be addressed to fully realize the compound's clinical potential. Ongoing research is focused on structural modifications to improve these pharmacokinetic properties, as well as on the identification of new biological targets. Collaborative efforts between academia and industry are expected to accelerate the translation of these findings into clinically viable drugs.

In conclusion, Methyl 5-chloroimidazo[1,5-a]pyridine-6-carboxylate (CAS: 1168090-92-3) represents a promising scaffold in medicinal chemistry, with demonstrated applications in kinase inhibition and anti-inflammatory therapy. Recent advancements in its synthesis and biological evaluation have expanded its potential utility, while also highlighting areas for further investigation. As research in this area continues to evolve, this compound is likely to play an increasingly important role in the development of novel therapeutics for a range of diseases.

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