4-((tert-Butoxycarbonyl)amino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid
[CAS# 956460-96-1]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives
• Name: 4-((tert-Butoxycarbonyl)amino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid
• Synonyms: 4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid
• Molecular Formula: C₁₇H₂₃N₅O₄
• Molecular Weight: 361.40
• CAS Registry Number: 956460-96-1
• SMILES: CC(C)(C)OC(=O)NC1(CCN(CC1)C2=NC=NC3=C2C=CN3)C(=O)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.633, Calc.^*
• Boiling Point: 619.9±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 328.7±31.5 °C, Calc.^*

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

Discovery and Applications

4-((tert-Butoxycarbonyl)amino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid is a chemical compound that has garnered attention in the field of medicinal chemistry due to its unique structural features, which combine a piperidine ring with pyrrolo[2,3-d]pyrimidine and tert-butoxycarbonyl (Boc) functional groups. The Boc group is often used in the synthesis of amines and is a protective group that allows for selective reactions while preventing undesired interactions. The pyrrolo[2,3-d]pyrimidine ring system is a versatile scaffold, known for its biological activity, including its potential as a kinase inhibitor. The combination of these moieties in this compound suggests that it may exhibit potent biological effects, especially in drug discovery and development.

The synthesis of 4-((tert-butoxycarbonyl)amino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid typically involves the preparation of the piperidine core, followed by the introduction of the pyrrolo[2,3-d]pyrimidine fragment. The Boc group is often added to the amino group of the piperidine to protect it during synthesis, with subsequent deprotection steps used to reveal the active amine. Various synthetic methods, such as cyclization reactions or coupling reactions, are employed to link the different structural components efficiently. The carboxylic acid group plays a crucial role in making the compound more soluble and enhancing its ability to interact with biological systems.

This compound has potential applications in drug design, particularly in the development of small molecules targeting enzymes or receptors involved in critical biological processes. The pyrrolo[2,3-d]pyrimidine scaffold is known to exhibit significant activity as an inhibitor of protein kinases, which are implicated in various diseases, including cancer, neurodegenerative disorders, and inflammatory conditions. The piperidine ring and the carboxylic acid functionality may provide additional pharmacokinetic advantages, such as improved solubility and bioavailability.

By optimizing the structure of 4-((tert-butoxycarbonyl)amino)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxylic acid, researchers aim to improve its potency and selectivity, making it a promising candidate for further development as a therapeutic agent. Its ability to target specific biological pathways related to disease mechanisms positions it as an attractive lead compound for the design of novel drug candidates.

References

none