tert-Butyl (S)-3-amino-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
[CAS# 2212021-59-3]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: tert-Butyl (S)-3-amino-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
• Synonyms: 2-Methyl-2-propanyl (4S)-3-amino-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo[4,3-c]pyridine-5-carboxylate
• Molecular Formula: C₂₀H₂₇FN₄O₂
• Molecular Weight: 374.45
• CAS Registry Number: 2212021-59-3
• EC Number: 889-020-6
• SMILES: C[C@H]1C2=C(N(N=C2CCN1C(=O)OC(C)(C)C)C3=CC(=C(C(=C3)C)F)C)N

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 506.8±50.0 ºC 760 mmHg (Calc.)^*
• Flash point: 260.3±30.1 ºC (Calc.)^*
• Index of refraction: 1.595 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS09 Warning
• Hazard Statements: H410
• Precautionary Statements: P273-P391-P501

Discovory and Applicatios

tert-Butyl (S)-3-amino-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo\[4,3-c]pyridine-5-carboxylate is a complex nitrogen-containing heterocyclic compound that belongs to the pyrazolopyridine class. It incorporates several distinct functional groups and structural motifs that contribute to its chemical behavior and potential pharmacological relevance. The molecular structure includes a chiral center (denoted by the (S) configuration), a fused bicyclic heteroaromatic core, a tert-butyl ester group, and a substituted aryl ring.

This compound features a fused pyrazolo\[4,3-c]pyridine core, which is a bicyclic system combining a pyrazole ring and a pyridine ring. The structural rigidity and electron-rich nature of this fused ring system make it particularly attractive in medicinal chemistry, especially for targeting biological macromolecules such as kinases, GPCRs, and enzymes. The presence of nitrogen atoms in the heterocycle allows for multiple points of interaction through hydrogen bonding and π-stacking, aiding in receptor binding.

The 4-fluoro-3,5-dimethylphenyl substituent provides additional hydrophobic and electronic character. Fluorine substitution in pharmaceuticals is known to influence metabolic stability, membrane permeability, and binding affinity. Methyl groups at the 3- and 5-positions further enhance lipophilicity and can influence steric interactions within a biological binding pocket.

The tert-butyl ester moiety serves as a protecting group for the carboxylic acid during synthesis and may also contribute to increased compound stability or altered pharmacokinetic properties. It is commonly used in synthetic chemistry for its resistance to hydrolysis under basic conditions and its ease of removal under acidic conditions. This ester can be cleaved to yield the free carboxylic acid, which is often required for biological activity or further chemical modification.

The stereochemistry at the 3-position, indicated by the (S) designation, is crucial for the biological function of many chiral molecules. Enantiomers can display markedly different pharmacological profiles, including efficacy, toxicity, and metabolic fate. The introduction of chirality in this compound suggests its design for stereoselective biological activity, potentially improving its interaction with asymmetric biological targets such as enzymes or receptors.

While the specific discovery and application of this exact compound have not been widely documented in the general literature, compounds with similar fused pyrazolopyridine structures have been extensively studied in drug discovery programs. These include candidates for the treatment of inflammatory diseases, cancers, and neurological disorders. The pharmacophore formed by the pyrazolopyridine ring system, combined with tailored side chains like aryl substituents and alkyl esters, has proven effective in optimizing ligand-receptor interactions.

In the context of synthetic methodology, the preparation of such molecules typically involves multistep synthesis. Key steps often include the construction of the fused heterocycle via cyclization reactions, selective substitution on the aromatic ring, and the introduction of protecting groups such as tert-butyl esters. Advanced asymmetric synthesis or chiral resolution techniques are used to obtain the desired enantiomer.

Characterization of this compound relies on modern spectroscopic techniques. Proton and carbon-13 nuclear magnetic resonance (NMR) spectroscopy provide information on the aromatic and aliphatic protons and carbon atoms. High-resolution mass spectrometry (HRMS) confirms the molecular weight and composition. Infrared (IR) spectroscopy is useful for identifying functional groups like ester carbonyl and amino groups.

In summary, tert-butyl (S)-3-amino-2-(4-fluoro-3,5-dimethylphenyl)-4-methyl-2,4,6,7-tetrahydro-5H-pyrazolo\[4,3-c]pyridine-5-carboxylate is a structurally elaborate compound representative of modern medicinal chemistry design. It integrates stereochemistry, heterocyclic chemistry, and strategic functionalization, making it a potentially valuable scaffold for pharmaceutical or biochemical development.