4-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine
[CAS# 1703794-33-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Triazines
• Name: 4-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine
• Molecular Formula: C₁₀H₈ClN₅
• Molecular Weight: 233.66
• CAS Registry Number: 1703794-33-5
• SMILES: CN1C=C(C=N1)C2=CN3C(=C2)C(=NC=N3)Cl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.757, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

4-Chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine is a synthetic compound that belongs to the pyrrolo[2,1-f][1,2,4]triazine family, which is known for its diverse biological activities. The compound features a triazine core fused to a pyrrole ring, with a chloromethyl group at position 4 and a pyrazolyl group at position 6. This structure imparts a unique set of chemical and biological properties, making it a candidate for various applications in medicinal chemistry and materials science.

The discovery of 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine stemmed from the exploration of triazine derivatives for their potential as biologically active molecules. The incorporation of the pyrazole group was found to enhance the reactivity and stability of the compound, while the chloro group at position 4 provides further versatility for chemical modifications. This combination of features has made the compound an attractive scaffold for drug discovery, particularly in the development of kinase inhibitors and other bioactive molecules.

The synthesis of 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine is typically achieved through methods such as nucleophilic substitution or palladium-catalyzed coupling reactions. These synthetic routes allow for the selective introduction of the pyrazolyl group, which plays a key role in the biological activity of the compound. Researchers have also investigated various optimization strategies to improve yield and selectivity during the synthesis process.

In terms of application, 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine shows promise as a potential therapeutic agent. It is being explored for its ability to inhibit specific kinases involved in cellular signaling, a mechanism that is particularly relevant in the treatment of cancers and other diseases related to dysregulated cell growth. Additionally, the compound's chemical properties make it a candidate for use in advanced materials, such as organic semiconductors, where it could improve device performance.

As research continues, 4-chloro-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[2,1-f][1,2,4]triazine is likely to play a larger role in both the development of new therapeutic agents and the design of novel materials for electronics.

References

2020. Avapritinib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0223