4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid
[CAS# 641569-94-0]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid
• Molecular Formula: C₁₇H₁₄N₄O₂
• Molecular Weight: 306.32
• CAS Registry Number: 641569-94-0
• EC Number: 629-968-8
• SMILES: CC1=C(C=C(C=C1)C(=O)O)NC2=NC=CC(=N2)C3=CN=CC=C3

Properties

• Density: 1.3$+/-$0.1 g/cm³ Calc.^*
• Boiling point: 587.9$+/-$60.0 $degree$C 760 mmHg (Calc.)^*
• Flash point: 309.4$+/-$32.9 $degree$C (Calc.)^*
• Index of refraction: 1.676 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302+H312+H332-H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332

Discovery and Applications

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid is a heterocyclic aromatic compound that combines a substituted benzoic acid moiety with a fused pyrimidine–pyridine amino linkage. Compounds of this type are important in medicinal chemistry due to their potential for hydrogen bonding, π–π interactions, and enzyme or receptor binding. The molecule’s structure incorporates multiple nitrogen-containing heterocycles, which provide electron-rich sites for molecular recognition and functionalization, while the carboxylic acid group serves as a reactive handle for derivatization or salt formation. Structurally, the molecule consists of a benzoic acid ring with a methyl substituent at the 4-position and an amino group at the 3-position that bridges to a 4-(3-pyridinyl)-2-pyrimidinyl system. The pyrimidine ring is electron-deficient, enhancing its ability to act as a hydrogen-bond acceptor, while the pyridine ring contributes planarity and additional nitrogen-based coordination sites. The carboxylic acid group on the benzoic acid provides polarity, aqueous solubility, and the ability to form salts or esters for chemical modification. This combination of heterocycles and functional groups creates a scaffold suitable for interactions with enzymes, receptors, or nucleic acids. The synthesis of 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid generally involves nucleophilic aromatic substitution or amination reactions. A 4-(3-pyridinyl)-2-chloropyrimidine intermediate is reacted with 3-amino-4-methylbenzoic acid under controlled conditions to form the amino linkage between the heterocyclic system and the benzoic acid. Reaction parameters are optimized to prevent side reactions, such as multiple substitutions or hydrolysis of the carboxylic acid, ensuring the formation of the desired compound with high purity. In medicinal chemistry, derivatives of this compound are explored as enzyme inhibitors, receptor modulators, or ligands for nucleic acid targets. The amino bridge allows for hydrogen bonding with active site residues, while the pyrimidine and pyridine rings provide π–stacking interactions and electron density modulation that enhance binding affinity. The methyl group on the benzoic acid can influence steric orientation and lipophilicity, improving pharmacokinetic properties. The carboxylic acid group may also participate in ionic interactions with positively charged residues in biological targets, further increasing specificity and potency. Beyond pharmacological applications, 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid is used as a versatile intermediate in organic synthesis. The carboxylic acid group allows formation of esters, amides, or salts, while the heterocyclic amino linkage can be modified to produce libraries of derivatives with varied electronic and steric properties. This versatility enables the generation of functional molecules for structure–activity relationship studies or the construction of more complex heterocyclic systems. Overall, 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid represents a multifunctional heterocyclic scaffold combining a substituted benzoic acid with pyridine and pyrimidine moieties. Its hydrogen-bonding potential, π–π interaction capacity, and reactive carboxylic acid group make it valuable for medicinal chemistry, synthetic applications, and the development of bioactive compounds.

References

2016. Nilotinib. Pharmaceutical Substances.

2007. An Efficient Synthesis of Nilotinib (AMN107). Synthesis.
DOI: 10.1055/s-2007-983754