2-Amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide
[CAS 280773-17-3]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: 2-Amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide
• Molecular Formula: C₁₃H₁₂ClN₃O₂
• Molecular Weight: 277.71
• CAS Registry Number: 280773-17-3
• EC Number: 800-516-3
• SMILES: COC1=CC(=C(C=C1)N)C(=O)NC2=NC=C(C=C2)Cl

Properties

• Density: 1.4$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 396.9$+/-$42.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 193.8$+/-$27.9 $degree$C (Calc.)^*
• Index of refraction: 1.671 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS08 Warning
• Risk Statements: H371
• Safety Statements: P260-P264-P270-P308+P316-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	2	H371

Discovery and Applications

2-Amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide is a substituted benzamide containing an amino group, a methoxy group, and a chloropyridinyl moiety. The compound belongs to a broader class of heteroaromatic benzamides that have attracted attention in medicinal chemistry because the benzamide framework is frequently employed in the design of biologically active molecules. The presence of both a pyridine ring and multiple functional groups provides opportunities for intermolecular interactions with biological targets, making compounds of this type useful intermediates and lead structures in pharmaceutical research.

The development of substituted benzamides as research compounds emerged from extensive investigations into structure-activity relationships involving aromatic amides. During the second half of the twentieth century, medicinal chemists increasingly explored the incorporation of heterocyclic rings such as pyridine into benzamide scaffolds. These modifications were found to influence physicochemical properties, receptor binding, enzyme interactions, and metabolic behavior. As a result, numerous chloropyridinyl-substituted benzamides were synthesized and evaluated in research programs aimed at identifying compounds with useful biological activity.

2-Amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide has been reported in the chemical and patent literature as a synthetic intermediate and research compound. The compound contains several structural features commonly used in medicinal chemistry. The benzamide linkage serves as a hydrogen-bond donor and acceptor, while the amino and methoxy substituents modify the electronic properties of the aromatic ring. The chloropyridinyl group introduces a heteroaromatic nitrogen atom together with a chlorine substituent, features frequently employed to influence binding affinity and selectivity in biologically active molecules.

The synthesis of compounds of this type generally involves formation of the amide bond between an appropriately substituted aminomethoxybenzoic acid derivative and a chloropyridinyl amine. Such synthetic strategies have been widely employed in pharmaceutical chemistry because they provide efficient access to diverse benzamide analogs for biological evaluation. The compound has therefore served as a useful building block in programs directed toward the discovery and optimization of more complex chemical entities.

A documented application of 2-amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide is its use as an intermediate in medicinal chemistry research. Patent publications and pharmaceutical development studies have described the preparation of structurally related benzamide derivatives for investigation as biologically active compounds. In such work, intermediates possessing amino, methoxy, and chloropyridinyl substituents are frequently transformed into more elaborate molecules through further functionalization reactions.

The compound has also been used in synthetic chemistry studies aimed at preparing libraries of heteroaromatic benzamides. The amino group present on the aromatic ring provides a convenient site for additional derivatization, allowing researchers to generate numerous analogs from a common precursor. This strategy has been widely employed in medicinal chemistry because it facilitates systematic evaluation of the effects of structural modification on biological properties.

In addition to its role as a synthetic intermediate, the compound has value in structure-activity relationship investigations. Research programs often require the preparation of closely related analogs to determine how specific substituents affect biological activity. Molecules containing the benzamide and chloropyridinyl motifs have therefore contributed to the broader understanding of heteroaromatic amide chemistry and its application in drug discovery.

The significance of 2-amino-N-(5-chloro-2-pyridinyl)-5-methoxybenzamide lies primarily in its use as a research and synthetic intermediate. Published chemical and patent literature demonstrates its role in the preparation of more complex heteroaromatic benzamide derivatives. Through such applications, the compound has contributed to medicinal chemistry efforts focused on the discovery and optimization of biologically active molecules.

References

2020. Expedient Approach to the Synthesis of Betrixaban. SynOpen.
DOI: 10.1055/s-0040-1707267

2017. Betrixaban. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0287