(4S)-2-(4-Fluoro-3,5-dimethylphenyl)-3-[3-(4-fluoro-1-methylindazol-5-YL)-2-oxoimidazol-1-YL]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-C]pyridine-5-carboxylic acid tert-butyl ester
[CAS 2212022-55-2]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: (4S)-2-(4-Fluoro-3,5-dimethylphenyl)-3-[3-(4-fluoro-1-methylindazol-5-YL)-2-oxoimidazol-1-YL]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-C]pyridine-5-carboxylic acid tert-butyl ester
• Synonyms: tert-butyl (4S)-2-(4-fluoro-3,5-dimethylphenyl)-3-[3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carboxylate
• Molecular Formula: C₃₁H₃₃F₂N₇O₃
• Molecular Weight: 589.64
• CAS Registry Number: 2212022-55-2
• SMILES: C[C@H]1C2=C(N(N=C2CCN1C(=O)OC(C)(C)C)C3=CC(=C(C(=C3)C)F)C)N4C=CN(C4=O)C5=C(C6=C(C=C5)N(N=C6)C)F

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

(4S)-2-(4-fluoro-3,5-dimethylphenyl)-3-[3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl]-4-methyl-6,7-dihydro-4H-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester is a highly complex, polyheterocyclic small molecule featuring multiple fused nitrogen-containing ring systems, fluorinated aromatic substituents, and a protected carboxylic acid in the form of a tert-butyl ester. The structure is characterized by significant conformational rigidity combined with multiple stereochemical elements and densely functionalized heteroaromatic regions.

The core of the molecule is a pyrazolo[4,3-c]pyridine framework, which is a fused bicyclic heteroaromatic system composed of a pyrazole ring fused to a partially saturated pyridine-derived ring. This scaffold contains multiple nitrogen atoms that contribute to electron distribution, hydrogen-bonding capacity, and heteroaromatic stabilization. The partial saturation in the 6,7-dihydro portion introduces conformational flexibility relative to a fully aromatic system, while still maintaining a defined bicyclic backbone.

At the 5-position of this core is a carboxylic acid functional group that is masked as a tert-butyl ester. The tert-butyl ester consists of a carbonyl group bonded to an oxygen atom bearing a bulky tert-butyl substituent. This protecting group significantly increases steric bulk and hydrophobicity, and it is commonly used in synthetic chemistry to temporarily mask carboxylic acids due to its stability under a variety of conditions and its ability to be removed under acidic conditions. The ester linkage is one of the key polar functional sites in the molecule, with the carbonyl oxygen acting as a hydrogen-bond acceptor.

The molecule contains multiple aromatic and heteroaromatic substituents. At the 2-position of the central scaffold is a 4-fluoro-3,5-dimethylphenyl group. This substituted phenyl ring introduces significant hydrophobic character and steric bulk. The fluorine substituent at the para position is strongly electron-withdrawing due to the high electronegativity of fluorine and the strength of the carbon–fluorine bond. Methyl groups at the 3 and 5 positions further increase hydrophobicity and influence the electronic distribution and steric environment of the aromatic ring.

At the 3-position of the core is a highly functionalized heteroaromatic substituent consisting of a 3-(4-fluoro-1-methylindazol-5-yl)-2-oxoimidazol-1-yl group. This portion contains multiple fused nitrogen-rich heterocycles, including an indazole ring system and an imidazolone-like moiety. Indazole is a bicyclic structure formed by fusion of benzene and pyrazole rings, containing two adjacent nitrogen atoms within the five-membered ring. The presence of a fluorine substituent and an N-methyl group on the indazole further modifies its electronic and steric properties.

The imidazolone fragment introduces a carbonyl-containing heterocycle with multiple nitrogen atoms capable of hydrogen-bond acceptance. The carbonyl group within this system is a key polar feature and contributes to intermolecular interaction capability. The combination of indazole and imidazolone rings creates a highly nitrogen-rich, electronically complex substituent.

The molecule contains multiple fluorinated aromatic systems. Carbon–fluorine bonds are highly polarized and chemically robust, and fluorination is known to strongly influence lipophilicity, metabolic stability, and electronic distribution across aromatic systems. In this structure, fluorine atoms are incorporated into both phenyl and indazole rings, contributing to a highly tuned electronic environment.

From a stereochemical perspective, the (4S) designation indicates a defined chiral center within the partially saturated bicyclic core. This stereochemistry controls the three-dimensional orientation of substituents and influences the overall spatial arrangement of the molecule. The presence of stereochemistry within a rigid polycyclic system can significantly affect conformational preferences and molecular recognition properties.

Physicochemically, the molecule exhibits a strong balance of hydrophobic and polar domains. The multiple aromatic rings and tert-butyl ester contribute substantial lipophilicity, while the heteroaromatic nitrogens and carbonyl groups introduce polarity and hydrogen-bond-accepting functionality. This combination results in a structurally amphiphilic compound with complex intermolecular interaction potential.

Chemically, the most reactive functional groups under appropriate conditions include the ester linkage, which can undergo hydrolysis under acidic or basic conditions, and the heteroaromatic carbonyl-containing systems, which can participate in hydrogen bonding or nucleophilic addition under specialized conditions. The fluorinated aromatic rings and fused heterocycles are generally stable under typical chemical environments.

Without specific verified literature describing this exact compound, no statements can be made regarding biological activity or application. Based solely on structural analysis, it is best described as a stereochemically defined, highly fused heteroaromatic system containing multiple fluorinated aromatic substituents, nitrogen-rich heterocycles, and a protected carboxylic acid, forming a rigid and electronically diverse molecular architecture.

References

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URL: https://patents.google.com/patent/US12365682B2

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URL: https://patents.google.com/patent/WO2025119206A1

2024. Substituted imidazoles as GLP-1 receptor agonists. US-12037339-B2 Grant Date: 2024-07-16.
URL: https://patents.google.com/patent/US12037339B2