Production Method 1

942947-94-6

73183-34-3

19798-80-2

944401-60-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: Dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane addu… Solvents: 1,4-Dioxane ;  6 h, 115 °C

Reference

Identification of NVP-BKM120 as a Potent, Selective, Orally Bioavailable Class I PI3 Kinase Inhibitor for Treating Cancer

Burger, Matthew T.; Pecchi, Sabina; Wagman, Allan; Ni, Zhi-Jie; Knapp, Mark; et al, ACS Medicinal Chemistry Letters, 2011, 2(10), 774-779

4-Chloro-pyridin-2-ylamine Raw materials

• 5-Bromo-4-chloropyridin-2-amine
• Bis(pinacolato)diborane

4-Chloro-pyridin-2-ylamine Preparation Products

• 4-Chloro-pyridin-2-ylamine (19798-80-2)
• 4-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine (944401-60-9)

• 1. The electric dipole moments of chloro-anilines and of some chloro-, bromo-, and nitro-substituted amino-pyridines in benzene and 1,4-dioxan solutions
  C. W. N. Cumper,A. Singleton J. Chem. Soc. B 1968 645
• 2. Identification and optimisation of a series of N-(4-anilino-2-pyridyl)acetamide activin receptor-like kinase 1 (ALK1) inhibitors
  Frederick W. Goldberg,Paula Daunt,Stuart E. Pearson,Ryan Greenwood,Matthew Grist,Judit é. Debreczeni Med. Chem. Commun. 2016 7 1204
• 3. Towards a RIOK2 chemical probe: cellular potency improvement of a selective 2-(acylamino)pyridine series
  Christopher B. Wang,álvaro Lorente-Macías,Carrow Wells,Julie E. Pickett,Alfredo Picado,William J. Zuercher,Alison D. Axtman RSC Med. Chem. 2021 12 129
• 4. The ultraviolet spectra of aniline, 2-, 3-, and 4-aminopyridines and of some of their derivatives in n-hexane, 1,4-dioxan, ethanol, and water solutions
  C. W. N. Cumper,A. Singleton J. Chem. Soc. B 1968 649
• 5. The versatility of non-heme diiron monooxygenase PmlABCDEF: a single biocatalyst for a plethora of oxygenation reactions
  Vytautas Petkevi?ius,Justas Vaitekūnas,Mikas Sadauskas,Fabian Peter Josef Schultes,Dirk Tischler,Rolandas Me?kys Catal. Sci. Technol. 2022 12 7293

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Aminopyridines and derivatives

Introduction to 4-Chloro-pyridin-2-ylamine (CAS No. 19798-80-2)

4-Chloro-pyridin-2-ylamine, with the chemical formula C?H?ClN?, is a significant intermediate in the pharmaceutical and agrochemical industries. This compound, identified by its CAS number 19798-80-2, has garnered attention due to its versatile applications in synthesizing various biologically active molecules. The presence of both chloro and amine functional groups makes it a valuable precursor for further chemical modifications, enabling the development of novel compounds with potential therapeutic benefits.

Thepyridin-2-ylamine moiety is particularly noteworthy, as it forms the backbone of many pharmacologically relevant structures. Pyridine derivatives are widely recognized for their role in medicinal chemistry, often serving as key components in drugs targeting neurological disorders, infectious diseases, and cancer. The introduction of a chlorine atom at the 4-position enhances the reactivity of the molecule, facilitating further functionalization through nucleophilic substitution reactions.

In recent years, 4-Chloro-pyridin-2-ylamine has been extensively studied for its utility in the synthesis of small-molecule inhibitors. For instance, researchers have explored its incorporation into kinase inhibitors, which are critical in oncology treatments. The chlorine substituent allows for selective modifications, enabling the tuning of binding affinity and selectivity against target proteins. This adaptability has made it a preferred building block in drug discovery pipelines.

Moreover, theCAS no 19798-80-2 compound has found applications in agrochemical formulations. Its structural features contribute to the development of herbicides and pesticides by enhancing bioavailability and metabolic stability. The ability to derivatize4-Chloro-pyridin-2-ylamine into more complex molecules has opened new avenues for crop protection strategies, addressing challenges such as pest resistance and environmental sustainability.

The synthesis of 4-Chloro-pyridin-2-ylamine typically involves chlorination reactions on pyridine derivatives or nucleophilic substitution of halogenated pyridines. Advanced synthetic methodologies, including catalytic hydrogenation and transition-metal-catalyzed cross-coupling reactions, have been optimized to improve yield and purity. These techniques are essential for ensuring that the final product meets the stringent requirements of pharmaceutical manufacturing.

Recent advancements in computational chemistry have further highlighted the importance of 4-Chloro-pyridin-2-ylamine in drug design. Molecular modeling studies indicate that modifications to this scaffold can significantly alter pharmacokinetic properties, such as solubility and metabolic clearance. By leveraging these insights, medicinal chemists can design analogs with improved pharmacological profiles, reducing side effects and enhancing therapeutic efficacy.

Thepyridin-2-ylamine derivative also plays a role in material science applications beyond pharmaceuticals. Its ability to form coordination complexes with metal ions makes it useful in catalysis and sensor development. Researchers have demonstrated its efficacy in designing luminescent materials and electrochemical sensors, showcasing its broad utility across multiple scientific disciplines.

In conclusion, 4-Chloro-pyridin-2-ylamine (CAS No. 19798-80-2) is a multifaceted compound with significant implications in pharmaceuticals, agrochemicals, and materials science. Its structural versatility and reactivity make it a cornerstone in synthetic chemistry, driving innovation in drug discovery and industrial applications. As research continues to uncover new uses for this molecule, its importance is expected to grow further.

• 20151-42-2(4-Chloroquinolin-2-amine)
• 364757-36-8(1-(4-Chloropyridin-2-yl)hydrazine)
• 188577-69-7(3,4-Dichloropyridin-2-amine)
• 6309-00-8(4-chloropyridine-2,6-diamine)
• 1184843-26-2(8-Chloroisoquinolin-3-amine)
• 188577-68-6(4,5-Dichloropyridin-2-amine)
• 39620-04-7(3-chloropyridin-2-amine)
• 1072-98-6(2-Amino-5-chloropyridine)
• 202216-99-7(4-Chloropyridin-2-amine hydrochloride)
• 782439-26-3(4-chloro-N-methylpyridin-2-amine)