tert-Butyl (S)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-3-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
[CAS# 2212021-61-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: tert-Butyl (S)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-3-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
• Molecular Formula: C₂₃H₂₈FN₅O₃
• Molecular Weight: 441.50
• CAS Registry Number: 2212021-61-7
• EC Number: 895-461-5
• SMILES: C[C@H]1C2=C(N(N=C2CCN1C(=O)OC(C)(C)C)C3=CC(=C(C(=C3)C)F)C)N4C=CNC4=O

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319
• Precautionary Statements: P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Discovory and Applicatios

tert-Butyl (S)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-3-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate is a synthetic compound notable for its structural complexity and significant biological potential. This molecule belongs to the class of pyrazolopyridine derivatives, which have garnered attention due to their broad range of pharmacological applications. The combination of functional groups in its structure, such as the pyrazolopyridine core, imidazolyl substituent, and fluorinated aromatic ring, contributes to its versatile chemical behavior and biological activity.

The discovery of this compound emerged from efforts to design new pharmacophores with potential therapeutic uses, particularly in fields related to inflammation, oncology, and neurological disorders. Early research explored the pyrazolopyridine scaffold for its ability to modulate biological targets, and the inclusion of fluorinated aromatic rings was found to enhance bioactivity and metabolic stability. Researchers sought to optimize these structures by introducing steric and electronic modifications, leading to the synthesis of this specific molecule.

The synthesis of tert-butyl (S)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-3-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate typically involves multi-step organic transformations. A key step is the condensation of a suitably functionalized pyrazole derivative with an imidazolyl-containing intermediate. Protecting groups, such as the tert-butyl ester, are used to facilitate the synthesis and ensure the stability of the final product. The stereochemistry of the molecule is controlled through chiral catalysts or auxiliaries to achieve the desired (S)-configuration.

This compound has shown promise in preclinical studies for its potential as an inhibitor of kinases and other enzymes relevant to disease pathways. Pyrazolopyridine derivatives are known to interact with cellular signaling pathways, making them candidates for drug development in cancer and inflammatory diseases. The fluorine atoms and methyl groups enhance the compound's ability to penetrate cell membranes and improve binding affinity to target proteins. Research continues to explore its pharmacokinetics, efficacy, and safety profiles, aiming to translate these findings into clinical applications.

The ongoing development of such compounds highlights the importance of structure-based drug design and the role of synthetic organic chemistry in discovering new therapeutic agents. The structural complexity and biological relevance of tert-butyl (S)-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-3-(2-oxo-2,3-dihydro-1H-imidazol-1-yl)-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate exemplify the advances being made in medicinal chemistry.