944317-54-8 | 4-Methyl-6-trifluoromethyl-pyridin-3-ylamine

CAS:944317-54-8 | 4-Methyl-6-trifluoromethyl-pyridin-3-ylamine,Description

“4-Methyl-6-(trifluoromethyl)pyridin-3-amine” is a compound with the molecular formula CHFN. It is a key intermediate in the atroposelective synthesis of the potent KRAS G12C covalent inhibitor divarasib (GDC-6036).

Synthesis Analysis

The synthesis of this compound involves several steps. For instance, one method involves the reaction of hydrazine with ethylhydrazine or propan-2-ylhydrazine, followed by a reaction with p-TsOH and then with pyridyl boronic acid. Another method involves the use of dichloropyrimidines and Suzuki coupling with boronic acids or esters.

Chemical Reactions Analysis

The chemical reactions involving this compound are complex and involve multiple steps. For example, one reaction involves the transformation of the chloride into a 4H-pyran-4-one intermediate. Another reaction involves the ring cleavage methodology for the synthesis of 2-alkyl/aryl 3-electron-withdrawing groups.

Physical And Chemical Properties Analysis

This compound has a molecular weight of 176.14. It is a solid at room temperature. The InChI key for this compound is GLJGKHHMJXKHPG-UHFFFAOYSA-N.

Scientific Research Applications

Synthesis and Structure Analysis

• Polynuclear Spin Crossover Complexes : In the field of inorganic chemistry, 4-Methyl-6-(trifluoromethyl)pyridin-3-amine has been used in synthesizing tetranuclear compounds with spin crossover properties. These compounds, featuring iron(II) atoms, demonstrate changes in spin state, influenced by structural modifications and temperature changes (Boldog et al., 2009).

Anticancer Research

• Potential Anticancer Agents : A range of derivatives of 4-Methyl-6-(trifluoromethyl)pyridin-3-amine have been synthesized and evaluated for anticancer activity. These novel alkyl amide functionalized compounds showed promising bioactivity against various cancer cell lines, indicating potential therapeutic applications (Chavva et al., 2013).

Synthetic Chemistry Applications

• Complex Metal Fluorides : In the domain of fluorine chemistry, 4-Methyl-6-(trifluoromethyl)pyridin-3-amine is involved in reactions with complex metal fluorides like caesium tetrafluorocobaltate(III). This process leads to the formation of various fluorinated compounds, showcasing its utility in synthetic chemistry (Plevey et al., 1982).

Catalysis and Polymerization

• Catalysis in Aryl-Cl Activation : The compound has been used in synthesizing aminopyridinato complexes, which are effective in activating aryl chlorides. These complexes demonstrate notable catalytic activities, especially in Suzuki cross-coupling reactions (Deeken et al., 2006).

Herbicidal Research

• Cellulose Biosynthesis Inhibition : In agricultural chemistry, derivatives of 4-Methyl-6-(trifluoromethyl)pyridin-3-amine have been identified as inhibitors of cellulose biosynthesis in plants. Additionally, upon exposure to UV-B light, these compounds transform into inhibitors of the enzyme phytoene desaturase, indicating dual herbicidal action (Wakeham et al., 2021).

Safety And Hazards

This compound is classified as harmful and is associated with several hazard statements including H302, H315, H319, and H335. Precautionary measures include avoiding breathing dust/fume/gas/mist/vapors/spray and washing thoroughly after handling.

Future Directions

Trifluoromethylpyridine (TFMP) derivatives, which include this compound, are used in the agrochemical and pharmaceutical industries. More than 20 new TFMP-containing agrochemicals have acquired ISO common names, and several TFMP derivatives are also used in the pharmaceutical and veterinary industries. It is expected that many novel applications of TFMP will be discovered in the future.

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