2-[3-(tert-butoxycarbonylaminomethyl)phenyl]-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid
[CAS# 640287-99-6]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 2-[3-(tert-butoxycarbonylaminomethyl)phenyl]-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid
• Molecular Formula: C₁₇H₁₈F₃N₃O₄
• Molecular Weight: 385.34
• CAS Registry Number: 640287-99-6
• SMILES: CC(C)(C)OC(=O)NCC1=CC(=CC=C1)N2C(=CC(=N2)C(F)(F)F)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.545, Calc.^*
• Boiling Point: 531.6±50.0 ºC (760 mmHg), Calc.^*
• Flash Point: 275.3±30.1 ºC, Calc.^*

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

Discovory and Applicatios

2-[3-(tert-butoxycarbonylaminomethyl)phenyl]-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid is a chemical compound that has gained attention for its potential applications in medicinal chemistry and materials science. This compound features a pyrazole ring, which is a five-membered heterocyclic structure, along with a trifluoromethyl group at the 5-position, a carboxylic acid at the 3-position, and a tert-butoxycarbonyl (Boc) protected amine group at the 3-position of the phenyl group. These structural features contribute to its chemical stability, bioactivity, and the ability to undergo further functionalization, making it a versatile candidate in drug development and chemical synthesis.

The pyrazole core in this compound is known for its biological activity, particularly its ability to interact with enzymes, receptors, and other biological macromolecules. The introduction of the trifluoromethyl group enhances the lipophilicity of the molecule, which can improve its membrane permeability, an important factor for compounds aimed at targeting intracellular processes. The Boc group, which serves as a protective group for the amine, allows for selective deprotection during later stages of synthesis, facilitating the generation of more reactive intermediates for further chemical modifications or conjugation to other bioactive molecules.

The synthesis of 2-[3-(tert-butoxycarbonylaminomethyl)phenyl]-5-trifluoromethyl-2H-pyrazole-3-carboxylic acid generally involves the formation of the pyrazole ring, followed by the selective introduction of the trifluoromethyl group and the carboxylic acid functionality. The final step includes the incorporation of the Boc-protected amine group, which is typically introduced using standard amination techniques. This synthesis method enables the compound to be produced in a controlled manner, with a high degree of functional group selectivity, which is important for ensuring the desired biological activity.

Applications of this compound are primarily focused on drug discovery. The presence of the carboxylic acid group allows for potential interaction with biological receptors and enzymes, which could be useful in the development of small molecules targeting inflammatory pathways, metabolic disorders, or cancer. The trifluoromethyl group may enhance the compound's activity by increasing its stability in vivo and improving its pharmacokinetic properties. Additionally, the compound could be used as a building block for the synthesis of more complex molecules in the development of targeted therapies. Its ability to undergo further modifications makes it an attractive candidate for the development of drugs with specific mechanisms of action.

Further research is needed to fully understand the biological profile of this compound, including its pharmacodynamics, selectivity for biological targets, and toxicity profile. In vivo studies, as well as high-throughput screening assays, could help determine its potential for clinical use in various therapeutic areas.