Cas no 2152227-42-2 (2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide)

2-Chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide is a heterocyclic compound featuring a pyrimidine core substituted with a chloro group at the 2-position and a carboxamide linkage to a piperidin-4-yl moiety. This structure imparts versatility in medicinal chemistry, particularly as a key intermediate in the synthesis of biologically active molecules. The chloro group enhances reactivity for further functionalization, while the piperidine ring contributes to improved pharmacokinetic properties, such as solubility and bioavailability. Its rigid scaffold makes it valuable for designing inhibitors targeting enzymes or receptors. The compound’s well-defined synthetic route ensures high purity and consistency, supporting its use in drug discovery and development.
2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide structure
2152227-42-2 structure
Product Name:2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide
CAS No:2152227-42-2
MF:C10H13ClN4O
MW:240.689420461655
CID:5619480
PubChem ID:165766025
Update Time:2025-09-28

2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide Chemical and Physical Properties

Names and Identifiers

    • 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide
    • EN300-28317737
    • 2152227-42-2
    • Inchi: 1S/C10H13ClN4O/c11-10-13-5-7(6-14-10)9(16)15-8-1-3-12-4-2-8/h5-6,8,12H,1-4H2,(H,15,16)
    • InChI Key: HVWDAVHDYXNAPB-UHFFFAOYSA-N
    • SMILES: ClC1=NC=C(C=N1)C(NC1CCNCC1)=O

Computed Properties

  • Exact Mass: 240.0777887g/mol
  • Monoisotopic Mass: 240.0777887g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 237
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 0.6
  • Topological Polar Surface Area: 66.9?2

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Additional information on 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide

Introduction to 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide (CAS No. 2152227-42-2) and Its Emerging Applications in Chemical Biology and Medicinal Chemistry

2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide, identified by its CAS number 2152227-42-2, is a heterocyclic compound that has garnered significant attention in the fields of chemical biology and medicinal chemistry due to its versatile structural framework and potential biological activities. This compound belongs to the pyrimidine class of molecules, which are well-documented for their role in various pharmacological applications, including antiviral, anticancer, and immunomodulatory therapies. The presence of a chloro substituent at the 2-position and an amide linkage connected to a piperidine ring introduces unique reactivity and binding properties, making it a valuable scaffold for drug discovery initiatives.

The structural features of 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide contribute to its pharmacological relevance. The pyrimidine core is a common motif in nucleoside analogs, which are known for their ability to interfere with nucleic acid synthesis in pathogens. Additionally, the amide group at the 5-position provides a site for further chemical modifications, enabling the development of derivatives with enhanced specificity and efficacy. The piperidine moiety enhances solubility and metabolic stability, which are critical factors in drug design. These attributes have positioned this compound as a promising candidate for further investigation in therapeutic contexts.

In recent years, there has been a surge in research focused on pyrimidine derivatives due to their broad spectrum of biological activities. Specifically, compounds with chloro-substituted pyrimidines have been explored for their potential as kinase inhibitors, particularly in the treatment of cancers and inflammatory diseases. For instance, studies have demonstrated that such derivatives can modulate the activity of enzymes involved in cell proliferation and survival pathways. The amide group in 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide serves as a key interaction point with biological targets, allowing for the design of molecules that can selectively bind to disease-causing proteins.

One of the most compelling aspects of this compound is its utility as a building block in medicinal chemistry. The flexibility of the piperidine ring allows for conformational adjustments that can optimize binding affinity to biological targets. Furthermore, the chloro substituent at the 2-position can participate in hydrogen bonding or π-stacking interactions, enhancing molecular recognition. These features have led to its incorporation into various drug discovery campaigns aimed at developing novel therapeutics. For example, researchers have utilized this scaffold to create inhibitors targeting Janus kinases (JAKs), which play a crucial role in inflammatory responses and autoimmune diseases.

The synthetic accessibility of 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide is another factor that underscores its importance in pharmaceutical research. The compound can be synthesized through well-established organic reactions, including nucleophilic substitution and condensation reactions. This ease of preparation allows for rapid screening and optimization of derivatives, expediting the drug development process. Moreover, advances in synthetic methodologies have enabled the introduction of additional functional groups or modifications, further expanding its utility as a pharmacophore.

Recent studies have highlighted the potential of 2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide in addressing unmet medical needs. For instance, research has indicated that derivatives of this compound exhibit inhibitory effects on certain proto-oncogenes associated with cancer progression. By targeting these pathways, such molecules may offer therapeutic benefits without significant side effects observed with conventional treatments. Additionally, preclinical trials have shown promise in using these derivatives as immunomodulators, suggesting their potential application in managing chronic inflammatory conditions.

The chemical biology community has also leveraged this compound to explore novel mechanisms of action. Researchers have employed it as a tool compound to study enzyme inhibition and receptor binding dynamics. Its well-defined structure allows for precise modifications that can alter its interactions with biological targets, providing insights into drug-receptor interactions at a molecular level. Such studies are crucial for understanding how drugs exert their effects and for designing more effective therapeutics.

In conclusion,2-chloro-N-(piperidin-4-yl)pyrimidine-5-carboxamide (CAS No. 2152227-42-2) represents a significant advancement in pharmaceutical research due to its structural versatility and potential biological activities. Its incorporation into drug discovery pipelines has yielded promising candidates for treating cancers, inflammatory diseases, and other disorders. As research continues to uncover new applications for this compound and its derivatives,its importance is likely to grow, driving further innovation in chemical biology and medicinal chemistry.

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