tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate
[CAS# 1083057-14-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound
• Name: tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate
• Molecular Formula: C₁₇H₂₀N₂O₂
• Molecular Weight: 284.35
• CAS Registry Number: 1083057-14-0
• EC Number: 800-303-5
• SMILES: CC1=C(N=C(C=C1)N)C2=CC(=CC=C2)C(=O)OC(C)(C)C

Properties

• Solubility: Practically insoluble (0.045 g/L) (25 °C), Calc.^*
• Density: 1.119±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2015 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate is a synthetic organic compound that has gained attention for its potential applications in medicinal chemistry and organic synthesis. This compound is characterized by its unique structure, which combines a tert-butyl ester, a benzoate group, and a substituted pyridine ring. The discovery and subsequent application of tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate have been driven by its utility as an intermediate in the synthesis of more complex molecules, particularly in the pharmaceutical industry.

The discovery of tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate was part of a broader effort to develop new chemical scaffolds that could serve as building blocks for drug development. The compound's structure includes a tert-butyl ester, which is commonly used in organic synthesis as a protecting group for carboxylic acids. This ester group can be easily removed under mild conditions, making the compound versatile for further chemical modifications. Additionally, the amino group on the pyridine ring provides a reactive site for various functionalization reactions, allowing for the introduction of additional substituents that can enhance the biological activity of derived molecules.

In practical applications, tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate has been utilized as an intermediate in the synthesis of pharmaceutical compounds, particularly those targeting specific enzymes or receptors in the body. The combination of the benzoate and pyridine moieties in the compound's structure is particularly advantageous in drug design, as these groups are known to interact effectively with biological targets. The presence of the methyl group on the pyridine ring can also influence the compound's electronic properties, potentially enhancing binding affinity and selectivity for certain proteins.

One of the key applications of tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate is in the development of kinase inhibitors, a class of drugs that are widely used in cancer therapy. Kinase inhibitors work by blocking the activity of specific enzymes that are involved in cell signaling pathways, thereby preventing the uncontrolled cell proliferation that is characteristic of cancer. The structural features of tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate make it a suitable precursor for the synthesis of molecules that can inhibit kinases, particularly those involved in the regulation of cell growth and survival.

Beyond its use in drug development, tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate has also been explored in the field of materials science. Its ability to undergo further chemical transformations makes it a valuable starting material for the synthesis of functionalized polymers and other materials with specialized properties. For instance, by modifying the pyridine ring or the benzoate group, researchers can design materials with specific electronic, optical, or mechanical properties for use in various industrial applications.

The versatility of tert-Butyl 3-(6-amino-3-methylpyridin-2-yl)benzoate in both medicinal chemistry and materials science underscores its importance as a synthetic intermediate. Its discovery has opened up new possibilities for the efficient synthesis of complex molecules, contributing to the advancement of both drug development and the creation of novel materials. As research continues, this compound is likely to find even more applications, further cementing its role in modern organic chemistry.

References

2020. Synthetic Approaches to Contemporary Drugs that Contain the Cyclopropyl Moiety. Synthesis.
DOI: 10.1055/s-0039-1690058

2016. Lumacaftor. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-12-0083