20168-70-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
2-Diethylamino-5-nitropyridine is utilized as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with potential therapeutic applications. Its role in the agrochemical sector involves the creation of compounds that can be used in pest control and crop protection, enhancing agricultural productivity and sustainability.
Used in Dye and Pigment Production:
In the dye and pigment industry, 2-Diethylamino-5-nitropyridine serves as a vital component in the manufacturing process. Its chemical properties allow for the creation of a wide range of colors and hues, which are essential for various applications such as textiles, plastics, and printing inks.
Safety Considerations:
Given its classification as a nitroaromatic compound, 2-Diethylamino-5-nitropyridine requires special attention to safety during its handling and storage. Proper precautions must be taken to minimize the risk of accidents and ensure the well-being of those involved in its production and use.

Upstream product

• 4548-45-2 2-chloro-5-nitropyridine 
• 121-44-8 triethylamine 
• 3710-84-7 N-ethyl-N-hydroxy-ethanamine 
• 2530-26-9 3-nitropyridine 
• 109-89-7 diethylamine 
• 4487-59-6 2-bromo-5-nitropyridine 
• 456-24-6 2-Fluoro-5-nitropyridine 

Downstream Products

• 34392-84-2 2-diethylamino-5-amino pyridine 

Relevant academic research and scientific papers

Substitution reactions of 5-nitropyridine-2-sulfonic acid. A new pathway to 2,5-disubstituted pyridines

We have investigated reactions of 5-nitropyridine-2-sulfonic acid and its potassium salt in which substitution of the sulfonate group by oxygen, nitrogen and halogen nucleophiles has been attempted. By this approach, 2-methoxy-(95% yield), 2-ethoxy- (97%), 2-isopropoxy- (65%), 2-amino- (92%), 2- butylamino- (76%), 2-diethylamino- (62%), 2-ethylamino- (32%), 2-benzylamino- (77%), 2-(R-1-phenylethylamino)- (71%) and 2-chloro-5-nitropyridine (87%) have been obtained. No reactions were observed with phenols or anilines. With t-BuOH, 2-hydroxy-5-nitropyridine was formed together with 2-methylpropene.

Photoredox catalyzed dealkylative aromatic halogen substitution with tertiary amines

A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment are

Design, synthesis and biological evaluation N2-(2-alkyoxy-6-aliphatic aminopyridin-3-yl)-2,4-diaminepyrimidine derivatives bearing acylamino or DBTD ‘head’ as potential ALK inhibitors

Aiming to develop promising ALK inhibitors, two series of N2-(2-alkyoxy-6-aliphatic aminopyridin-3-yl)-2,4-diaminepyrimidine derivatives (22a-x and 23a-d) were designed according to scaffold hopping and bioisosterism principles. All compounds were efficiently synthesized by concise reactions and anti-proliferative activities on ALK-addicted H2228, Karpas299 cells and EGFR-expressive A549 cell were evaluated by MTT assay. Several compounds exhibited potential cytotoxic activities with IC50 values below 0.10 μM. Five compounds (22g, 22h, 22l, 22s and 23a) were selected for further enzymatic determination, resulting in the discovery of 22l against ALK and ALKL1196M with IC50 values of 2.1 nM and 3.8 nM. Particularly, western blot and cell apoptosis assays identified 22l as a promising ALK inhibitor, which was capable of obviously inhibiting cellular ALK activity and inducing cell apoptosis. Eventually, molecular docking modes of 22l with ALK confirmed structural basis in accordance with the SARs analysis.

5-azido-2-aminopyridine, a new nitrene/nitrenium ion photoaffinity labeling agent that exhibits reversible intersystem crossing between singlet and triplet nitrenes

The photochemistry of a new photoaffinity labeling (PAL) agent, 5-azido-2-(N,N-diethylamino)pyridine, was studied in aprotic and protic solvents using femtosecond-to-microsecond transient absorption and product analysis, in conjunction with ab initio multiconfigurational and multireference quantum chemical calculations. The excited singlet S1 state is spectroscopically dark, whereas photoexcitation to higher-lying singlet excited S2 and S3 states drives the photochemical reaction toward a barrierless ultrafast relaxation path via two conical intersections to S 1, where N2 elimination leads to the formation of the closed-shell singlet nitrene. The singlet nitrene undergoes intersystem crossing (ISC) to the triplet nitrene in aprotic and protic solvents as well as protonation to form the nitrenium ion. The ISC rate constants in aprotic solvents increase with solvent polarity, displaying a "direct" gap effect, whereas an "inverse" gap effect is observed in protic solvents. Transient absorption actinometry experiments suggest that a solvent-dependent fraction from 20% to 50% of nitrenium ions is generated on a time scale of a few tens of picoseconds. The closed-shell singlet and triplet nitrene are separated by a small energy gap in protic solvents. As a result, the unreactive triplet state nitrene undergoes delayed, thermally activated reverse ISC to reform the reactive closed-shell singlet nitrene, which subsequently protonates, forming the remaining fraction of nitrenium ions. The product studies demonstrate that the resulting nitrenium ion stabilized by the electron-donating 4-amino group yields the final cross-linked product with high, almost quantitative efficiency. The enhanced PAL function of this new azide with respect to the widely applied 4-amino-3-nitrophenyl azide is discussed.

Discovery and optimization of 2-phenyloxazole derivatives as diacylglycerol acyltransferase-1 inhibitors

In a discovery effort to find safe and effective DGAT-1 inhibitors, we have identified 2-phenyloxazole 4-carboxamide 1 as a conformationally constrained analog of a hydrazide hit, which was previously identified from high-throughput screening. Further optimization of this series has led to chemically more stable 2-phenyloxazole-based DGAT-1 inhibitor 25 with improved solubility, cell-based activity, and pharmacokinetic properties. Compound 25 also demonstrated in vivo efficacy in a diet-induced obesity (DIO) rat model.

Inhibitors of bruton's tyrosine kinase

This application discloses 6-Phenyl-imidazo[1,2-a]pyrazine derivatives according to generic Formulae I-V: wherein, variables Q, R, Y1, Y2, Y3, Y4, n, and m are defined as described herein, which inhibit Btk. The

C-N bond formation by the oxidative alkylamination of azines: Comparison of AgPy2MnO4 versus KMnO4 as oxidant

Reports on the successful oxidative alkylamination of azines by the S NH-reaction, with the use of alkylamines other than methylamine, are very scarce. Hitherto, the experimental limitation to extend oxidative animation of azines wit

ANTICANCER COMPOUNDS

This invention features compounds having formula (I): wherein, R1, R 2,R3, R4, R6, R7, T, X, and Y are as defined herein. This invention also features a method for treating cancer. The method includes administrating to a subject in need thereof a compound of formula (I).

Neuropeptide Y antagonists

The compound is a neuropeptide Y antagonist and is effective in treating feeding disorders, cardiovascular diseases and other physiological disorders.

The oxidative amination of 3-nitropyridines

3-Nitropyridine was reacted with ammonia or alkylamines and KMnO4 under several different conditions. Substitutions in the para position to the nitro group were obtained with high regioselectivity: with ammonia, 2-amino-5-nitropyridine (66%), w