(2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one
[CAS# 764667-65-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrazines
• Name: (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one
• Synonyms: (2Z)-1-[3-(Trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-4-(2,4,5-trifluorophenyl)butane-1,3-dione
• Molecular Formula: C₁₆H₁₂F₆N₄O₂
• Molecular Weight: 406.28
• CAS Registry Number: 764667-65-4
• EC Number: 619-997-4
• SMILES: C1CN2C(=NN=C2C(F)(F)F)CN1C(=O)CC(=O)CC3=CC(=C(C=C3F)F)F

Properties

• Density: 1.6±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.58, Calc.^*
• Boiling Point: 513.9±60.0 °C (760 mmHg), Calc.^*
• Flash Point: 264.6±32.9 °C, Calc.^*

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

Safety Data

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

Discovery and Applications

The compound (2Z)-4-Oxo-4-[3-(trifluoromethyl)-5,6-dihydro-[1,2,4]triazolo[4,3-a]pyrazine-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-one is a complex organic molecule that combines multiple functional groups and a significant degree of fluorination. It falls within the broader class of heterocyclic compounds, which are characterized by their incorporation of atoms like nitrogen and oxygen into their ring structures. This particular molecule contains a triazole ring, a pyrazine ring, and is heavily substituted with trifluoromethyl groups on the aromatic rings, making it a fluorinated heterocyclic compound.

The discovery and synthesis of compounds like this one, especially those containing both trifluoromethyl and heterocyclic moieties, have been an area of interest in medicinal and materials chemistry due to their potential for various bioactivities and their influence on the properties of organic materials. The trifluoromethyl group is known for enhancing the lipophilicity and metabolic stability of molecules, making such compounds valuable in the pharmaceutical industry.

In particular, fluorinated compounds like this one are often explored for their activity in drug discovery, especially as potential antifungal, antiviral, or anticancer agents, owing to the chemical stability imparted by the fluorine atoms. The presence of the triazole and pyrazine rings may suggest potential activity in areas related to enzyme inhibition or receptor binding, as these structural motifs are frequently observed in biologically active molecules.

Moreover, the chemical structure of this compound is highly specific and suggests that it could be used in the development of materials with unique electronic or optical properties, as well as in agricultural chemicals. For instance, compounds with fluorine atoms in specific positions are often studied for their utility as herbicides or pesticides due to their ability to interfere with biochemical pathways in plants or microbes.

Research into this molecule would typically focus on synthesizing it via well-established methods for creating fluorinated heterocycles and testing it in various biological assays to identify any pharmacological properties. Synthesis often involves reactions like nucleophilic substitution or condensation reactions to form the heterocyclic rings, followed by fluorination to introduce the trifluoromethyl groups.

Given the complexity of the structure, with both a triazole and pyrazine ring incorporated into the molecular backbone, the synthesis and study of this compound would contribute to the growing body of research in fluorinated heterocycles and their diverse applications in fields ranging from pharmaceuticals to agriculture and materials science.

References

2007. Sitagliptin phosphate. Pharmaceutical Substances.

2015. Sitagliptin Synthesis. Science of Synthesis.

2016. Efficient Enantioselective Biocatalytic Production of a Chiral Intermediate of Sitagliptin by a Newly Filamentous Fungus Isolate. Applied Biochemistry and Biotechnology, 180(5).
DOI: 10.1007/s12010-016-2125-5