58381-05-8 | 5-Fluoro-2-methoxy-4-pyridinamine

CAS:58381-05-8 | 5-Fluoro-2-methoxy-4-pyridinamine,Description

The compound of interest, 5-Fluoro-2-methoxypyridin-4-amine, is a fluorinated pyridine derivative. Fluorinated pyridines are important in medicinal chemistry due to their potential biological activities and their use as building blocks in pharmaceuticals. The presence of a methoxy group and an amino group in the pyridine ring can significantly alter the chemical and physical properties of the compound, potentially leading to various applications in drug design and development.

Synthesis Analysis

The synthesis of related fluoropyridines has been reported using different methods. For instance, an efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction mediated by tetrabutylammonium fluoride (TBAF) under mild conditions has been described. This method is general for 2- or 4-nitro-substituted pyridines. Similarly, the synthesis of 2-Amino-5-(3-fluoro-4-methoxyphenyl)thiophene-3-carbonitrile, a related compound, has been achieved using the Gewald synthesis technique, followed by treatment with 1,3-disubstituted pyrazole-4-carboxaldehyde to obtain novel Schiff bases. These methods highlight the versatility of synthetic approaches available for fluorinated pyridines and their derivatives.

Molecular Structure Analysis

The molecular structure of fluoropyridine derivatives is typically confirmed using various analytical techniques such as IR, 1H NMR, 13C NMR, and mass spectrometry. These techniques provide detailed information about the substitution pattern on the pyridine ring and the presence of functional groups such as the methoxy and amino groups.

Chemical Reactions Analysis

Fluoropyridines can undergo various chemical reactions, including denitration to form hydroxy- and methoxypyridines. The presence of electron-withdrawing or electron-donating groups on the pyridine ring can influence the reactivity and the outcome of these reactions. For example, the synthesis of 5-bromo-2-methoxy-6-methylaminopyridine-3-carboxylic acid involved a series of reactions including methoxylation, oxidation, and nucleophilic substitution.

Physical and Chemical Properties Analysis

The physical and chemical properties of fluoropyridines are influenced by the substituents on the pyridine ring. The introduction of a methoxy group can affect the compound's biochemical potency and cellular penetration, as seen in the case of 5-methoxy- and 5-hydroxy-6-fluoro-1,8-naphthyridone-3-carboxylic acid derivatives. The presence of a fluorine atom can enhance the compound's stability and lipophilicity, which are desirable traits in drug development.

Scientific Research Applications

Pyridine Nucleosides Synthesis

5-Fluoro-2-methoxypyridin-4-amine has been utilized in the synthesis of various pyridine nucleosides, such as 5-fluorouracil derivatives. Nesnow and Heidelberger (1973, 1975) demonstrated the conversion of 5-Fluoro-2-methoxypyridin-4-amine into compounds like 4-deoxy-5-fluoro-3-deazauridine and 5-fluoro-3-deazacytidine. These compounds are of interest due to their potential applications in cancer research and treatment (Nesnow & Heidelberger, 1973); (Nesnow & Heidelberger, 1975).

Development of Kinase Inhibitors

In the field of kinase inhibitor development, 5-Fluoro-2-methoxypyridin-4-amine serves as a key intermediate. Wada et al. (2012) explored its use in synthesizing novel 2,4-disubstituted-5-fluoropyrimidines, a molecular core seen in many anticancer agents (Wada et al., 2012).

Antitumor Agents Synthesis

Tsuzuki et al. (2004) investigated the structure-activity relationships of compounds derived from 5-Fluoro-2-methoxypyridin-4-amine for potential antitumor applications. They found that specific substitutions at various positions significantly influenced the cytotoxic activity against tumor cell lines (Tsuzuki et al., 2004).

Catalyst-Free Amination Reactions

The compound has also been used in catalyst-free amination reactions. Abel et al. (2015) explored its reactions with adamantane amines, demonstrating its reactivity and potential for creating diverse aminopyridines (Abel et al., 2015).

Synthesis of Fluorinated Compounds

In the synthesis of fluorinated compounds, which are important in medicinal chemistry, 5-Fluoro-2-methoxypyridin-4-amine plays a significant role. For example, its derivatives have been synthesized for potential use as herbicides (Johnson et al., 2015).

Safety And Hazards

The compound is labeled with the GHS07 pictogram and has the signal word "Warning". It has hazard statements H302, H315, H319, H335, indicating that it is harmful if swallowed, causes skin irritation, causes serious eye irritation, and may cause respiratory irritation.

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