Tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate
[CAS# 1198408-35-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Piperidines
• Name: Tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate
• Synonyms: 4-(6-Amino-3-pyridyl)-1-Boc-piperidine
• Molecular Formula: C₁₅H₂₃N₃O₂
• Molecular Weight: 277.36
• CAS Registry Number: 1198408-35-3
• EC Number: 127-372-8
• SMILES: CC(C)(C)OC(=O)N1CCC(CC1)C2=CN=C(C=C2)N

Properties

• Density: 1.1±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.553, Calc.^*
• Boiling Point: 422.8±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 209.5±28.7 °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-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovery and Applications

Tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate is a chemical compound that contains a piperidine core substituted with a 6-aminopyridinyl group and a tert-butyl carbamate (Boc) protecting group. This structure is commonly used as an intermediate in the synthesis of bioactive molecules, particularly in medicinal chemistry and drug discovery.

The piperidine ring system is widely recognized for its role in pharmaceutical compounds due to its conformational stability and ability to interact with biological targets. The presence of the 6-aminopyridinyl moiety enhances the compound’s potential for binding to specific receptors or enzymes. The Boc protecting group provides stability during synthetic transformations, allowing selective modifications at other functional sites.

Applications of tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate are primarily found in the development of pharmaceuticals and advanced organic synthesis. It serves as a precursor for small-molecule inhibitors, receptor ligands, and other drug-like compounds. The compound’s structural features make it valuable in the design of kinase inhibitors, central nervous system agents, and anti-inflammatory drugs.

In synthetic chemistry, this compound is used in multi-step organic syntheses where selective deprotection of the Boc group enables further derivatization. Researchers utilize it to construct complex molecular frameworks that mimic biologically active scaffolds.

The importance of tert-butyl 4-(6-aminopyridin-3-yl)piperidine-1-carboxylate lies in its utility as a versatile intermediate rather than as a final active pharmaceutical ingredient. It continues to be an important building block in the development of novel therapeutic agents and chemical tools for biomedical research.

References

2021. Treating cancers with a cyclin-dependent kinase inhibitor. WO-2022261643-A1

2020. A chemical-enzymatic method for preparing key intermediates of CDK4/6 inhibitors. CN-112575044-A

2020. Cdk inhibitors. WO-2022113003-A1