13160-07-1

Basic information

• Product Name: N-(2-Pyridyl)nicotinamide
• Synonyms: N-(2-Pyridyl)nicotinamide;N-(2-Pyridinyl)-3-pyridinecarboxamide;N-(pyridin-2-yl)nicotinamide;N-pyridin-2-ylpyridine-3-carboxamide
• CAS NO: 13160-07-1
• Molecular Formula: C11H9N3O
• Molecular Weight: 199.212
• Mol File: 13160-07-1.mol

Chemical Properties

• Melting Point: 139-142 ºC
• Boiling Point: 286 ºC
• Flash Point: 127 ºC
• Appearance: /
• Density: 1.287
• Vapor Pressure: 0.0027mmHg at 25°C
• Refractive Index: 1.658
• Storage Temp.: 2-8°C
• CAS DataBase Reference: N-(2-Pyridyl)nicotinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Pyridyl)nicotinamide(13160-07-1)
• EPA Substance Registry System: N-(2-Pyridyl)nicotinamide(13160-07-1)

Safety Data

• Hazardous Substances Data: 13160-07-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-(2-Pyridyl)nicotinamide is used as a research compound for its potential therapeutic applications, particularly as an inhibitor of the enzyme poly(ADP-ribose)polymerase (PARP). This enzyme plays a crucial role in DNA repair and cell death, and its inhibition can lead to the development of new treatments for various diseases, including cancer.
Used in Medicinal Chemistry:
N-(2-Pyridyl)nicotinamide is used as a chelating agent for metal ions in medicinal chemistry. Its ability to bind metal ions can be utilized in the development of drugs that target metal-dependent enzymes or processes, potentially leading to novel therapeutic agents.
Used in Chemical Applications:
Due to its unique molecular structure and potential biological activities, N-(2-Pyridyl)nicotinamide may also have applications in various chemical fields, such as the synthesis of new compounds, development of analytical methods, or as a reagent in chemical reactions.

InChI:InChI=1/C11H9N3O/c15-11(9-4-3-6-12-8-9)14-10-5-1-2-7-13-10/h1-8H,(H,13,14,15)

Upstream product

• 504-29-0 2-aminopyridine 
• 59-67-6 nicotinic acid 
• 10400-19-8 3-pyridinecarbonyl chloride 
• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 699-98-9 Pyridine-2,3-dicarboxylic anhydride 
• 109-04-6 2-bromo-pyridine 
• 98-92-0 nicotinamide 
• 109-09-1 2-chloropyridine 
• 500-22-1 3-pyridinecarboxaldehyde 
• 626-55-1 3-Bromopyridine 
• 13939-06-5 molybdenum hexacarbonyl 
• 1120-90-7 3-iodopyridine 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1374639-87-8 phenyl (2-(pyridin-3-yl)imidazo[1,2-a]pyridin-3-yl)methanone 

Relevant articles and documents

1H and 13C NMR spectral studies of conformation of some N-(2-pyridinyl)-3-pyridinecarboxamides

The 1H and 13C NMR spectra of N-(2-pyridinyl)-, N-(4-methyl2-pyridinyl)-, and N-(6-methyl-2-pyridinyl)-3-pyridinecarboxamides (1-3, respectively) and 3-pyridinecarboxamide (4) in different solvents have been analysed using COSY, HETCOR, chemical shift and coupling constant correlations. The conformations of 1-4 have been obtained by utilizing the NMR spectra, NOE experiments and MINDO/3 calculations. In dilute solutions, the 2-pyridyl ring is coplanar with the amide group while the 3-pyridyl ring is apparently not. Compounds 1-3 dimerize through cooperative hydrogen bonding in concentrated CDCl3 solution (approximately 0.1 M) and the structure of the dimer resembles some of the DNA base-pairs. Hydrogen bonding between N-H and the solvent molecules hinders dimerization in (CD3)2CO and CD3CN.

Establishing supramolecular control over solid-state architectures: A simple mix and match strategy

With the help of robust principles of crystal engineering, it is possible to construct co-crystals where two or more different molecular entities coexist in the same crystalline lattice; the supramolecular assembly is driven by noncovalent interactions, most commonly by hydrogen bonds. We have synthesized two ditopic amide based ligands (N-(4-pyridin-2-yl)isonicotinamide) and (N-(3-pyridin-2-yl)nicotinamide) and systematically established their binding preferences when faced with aliphatic dicarboxylic acids with an odd and even number of carbon atoms. Each ligand was co-crystallized with four odd and four even-chain dicarboxylic acids, and 13/16 reactions produced crystals suitable for single-crystal structure determination. On the basis of these results, it is clear that carefully selected systems can be manipulated to produce assemblies in the solid state with very precise control over topology and dimensionality. These ligands can be made to produce either 0-D or 1-D architectures simply by fine-tuning the choice of co-crystallizing agent in the supramolecular synthesis. This mix-and-match strategy allows us to mimic the reliability and versatility of covalent synthesis, in terms of successfully preparing a target with predetermined connectivity and metrics.

Aminocarbonylation of N -Containing Heterocycles with Aromatic Amines Using Mo(CO) 6

We describe herein the palladium-catalyzed aminocarbonylation of nitrogen-containing heterocycles with aniline derivatives using molybdenum hexacarbonyl as a CO solid source, expanding the scope of the limited examples. This method is compatible with a variety of substitutions on the aniline moiety. The simple reaction conditions include easily available Pd(dppf)Cl 2 catalyst, DBU as base in DMF at 120 °C for 3 hours in sealed tube thereby leading to the isolation of 21 compounds with yields ranging from 18 to 82%. We also show that double aminocarbonylation reactions are possible in satisfactory yields regarding both coupling partners.

Mapping out the Relative Influence of Hydrogen and Halogen Bonds in Crystal Structures of a Family of Amide-Substituted Pyridines

The simultaneous use of hydrogen bonds and halogen bonds in crystal engineering strategies has previously been employed in order to generate new solid forms with applications in e.g. pharmaceutical and agrochemical industries. Unfortunately, it is not eas

Towards a sustainable synthesis of amides: chemoselective palladium-catalysed aminocarbonylation of aryl iodides in deep eutectic solvents

A palladium-catalysed aminocarbonylation of (hetero)aryl iodides has, for the first time, been accomplished in deep eutectic solvents as environmentally benign and recyclable media, under mild conditions. The reactions proceeded with a good substrate scope, and a variety of amides have been synthesized in yields up to 98%.

Microwave-assisted heteropolyanion-based ionic liquid promoted sustainable protocol to N-heteroaryl amides via N-directing dual catalyzed oxidative amidation of aldehydes

A sustainable procedure for the synthesis of N-heteroaryl amides directly from oxidative amidation of aldehydes catalyzed by heteropolyanion-based ionic liquids under microwave-promoted conditions has been reported. The transformation has proven to tolerate a wide range of aldehydes and amino heterocycles with different functional groups. Moderate to excellent yields, solvent-free media, operational simplicity and reusability of catalysts are the main highlights. Furthermore, the proposed N-directing dual-catalysis mechanistic pathway was briefly investigated in this report.

Copper-catalysed amidation of 2-chloro-pyridines

The simple and inexpensive N,N-dimethylcyclohexane-1,2-diamine/CuI catalytic system provides a versatile, easy and efficient access to an array of N-(2-pyridin-2-yl)-amides from 2-chloro-pyridine derivatives. The Royal Society of Chemistry 2013.

Toward versatile methods leading to highly functionalized imidazo[1,2-a]pyridines

A convenient and general method of preparation of polyfunctionalized imidazo[1,2-a]pyridines is reported. This methodology involves activation of secondary amides leading to the formation of the corresponding amidines 9. Different activating reagents have

Direct synthesis of primary arylamines via C-N cross-coupling of aryl bromides and triflates with amides

Aryl halides and triflates are coupled with primary amides to give the corresponding arylamines in the presence of a palladium catalyst, a suitable ligand, and a base. The catalyst system performs well for a large number of different substrates at 100-150 °C without solvent, and with low catalyst levels (0.12 mol % Pd). Nicotinamide might be useful as a nitrogen source in the Pd-catalyzed amination reaction.

Improved synthesis of N-substituted 2,3-pyridine-dicarboximides with microwave irradiation

The microwave-induced synthesis of N-substituted 2,3- pyridinedicarboximides (1) by means of two different approaches is presented. One involves direct N-alkylation of quinolinimide (2) (Method A) and the other, dehydrative condensation of quinolinic anhydride (4) and amines (Method B). Reactions resulted highly accelerated, with improved yields in relation to those obtained by conventional heating. The scope and limitations of each method and its variants are discussed.