182344-63-4

Basic information

• Product Name: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide
• Synonyms: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide;N-(5-Bromopyridin-2-Yl)Pivalamide;Propanamide, N-(5-bromo-2-pyridinyl)-2,2-dimethyl-
• CAS NO: 182344-63-4
• Molecular Formula: C₁₀H₁₃BrN₂O
• Molecular Weight: 257
• Mol File: 182344-63-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide(182344-63-4)
• EPA Substance Registry System: N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide(182344-63-4)

Safety Data

• Hazardous Substances Data: 182344-63-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide is employed as a building block in the development of new pharmaceuticals, leveraging its unique chemical structure to create novel drug candidates.
Used in Organic Synthesis:
In the field of organic synthesis, N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide serves as a key intermediate, facilitating the synthesis of more complex organic compounds for various applications.
Used in Chemical Reactions:
N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide is utilized as a reagent in chemical reactions, contributing to the formation of new organic molecules with potential applications in various industries, including materials science and medicinal chemistry.
Used in Drug Development:
N-(5-bromo-pyridin-2-yl)-2,2-dimethyl-propionamide may have potential applications in the development of new drugs, where its unique structure could be harnessed to target specific biological pathways or create innovative therapeutic agents.

Upstream product

• 1072-97-5 5-bromo-2-pyridylamine 
• 3282-30-2 pivaloyl chloride 
• 696-15-1 2-amino-5-bromopyridine N-oxide 
• 75-98-9 Trimethylacetic acid 
• 1538-75-6 2,2-dimethylpropanoic anhydride 

Downstream Products

• 1198408-35-3 6-amino-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1'-carboxylic acid tert-butyl ester 
• 1593268-01-9 N-(5-(3-(4-(tert-butyl)phenyl)prop-2-ynoyl)pyridin-2-yl)pivalamide 

Relevant articles and documents

Synthesis of micrococcinic acid

The first synthesis of micrococcinic acid (2) is described. The five rings of 2 are assembled from monocyclic precursors using four palladium-catalyzed biaryl coupling reactions.

Design, synthesis, and biological evaluation of novel Bcr-AblT315I inhibitors incorporating amino acids as flexible linker

Despite the success of imatinib in CML therapy through Bcr-Abl inhibition, acquired drug resistance occurs over time in patients. In particular, the resistance caused by T315I mutation remains a challenge in clinic. Herein, we embarked on a structural optimization campaign aiming at discovery of novel Bcr-Abl inhibitors toward T315I mutant based on previously reported dibenzoylpiperazin derivatives. We proposed that incorporation of flexible linker could achieve potent inhibition of Bcr-AblT315I by avoiding steric clash with bulky sidechain of Ile315. A library of 28 compounds with amino acids as linker has been developed and evaluated. Among them, compound AA2 displayed the most potent activity against Bcr-AblWT and Bcr-AblT315I, as well as toward Bcr-Abl driven K562 and K562R cells. Further investigations indicated that AA2 could induce apoptosis of K562 cells and down regulate phosphorylation of Bcr-Abl. In summary, the compounds with amino acid as novel flexible linker exhibited certain antitumor activities, providing valuable hints for the discovery of novel Bcr-Abl inhibitors to overcome T315I mutant resistance, and AA2 could be considered as a candidate for further optimization.

Discovery of novel Bcr-Abl inhibitors with diacylated piperazine as the flexible linker

Forty-two compounds (series 8, 9 and 10) incorporated with diacylated piperazine have been synthesized and evaluated as novel Bcr-Abl inhibitors based on 'six-atom linker'. Five of them, 8d, 8h, 8l, 10m and 10p, displayed potent Bcr-Abl inhibitory activity comparable with Imatinib. Moreover, compounds 8e, 10q, 10s, and 10u were potent Bcr-Abl inhibitors with IC50 values at the sub-micromolecular level. Most compounds exhibited moderate to high antiproliferative activity against K562 cells. In particular, compound 9e was the most promising Bcr-Abl inhibitor. Docking studies revealed that the binding modes of these compounds were similar with Imatinib. These compounds could be considered as promising lead compounds for further optimization.

Discovery of biphenyl-aryl ureas as novel VEGFR-2 inhibitors. Part 4: Exploration of diverse hinge-binding fragments

Abstract VEGFR-2 plays an essential role in angiogenesis and is an important target for cancer therapy. A series of biphenyl-aryl ureas were synthesized and evaluated as novel VEGFR-2 inhibitors. The pyridine, methylamine carbonyl pyridine and pivaloyl amide pyridine were introduced as novel hinge binding fragment. The majority of title compounds displayed potent VEGFR-2 inhibition. In particular, L1, L9, W14 and W15 exhibited significant enzymatic inhibitory activity with IC50 values of 0.36 nM, 0.22 nM, 0.15 nM and 0.14 nM. Compounds L1, L9 and W15 displayed potent antiproliferative activity against A549 and SMMC-7721 cells. SAR study suggested that incorporation of 3-trifluoromethyl and methylamine carbonyl on terminal pyridine could improve VEGFR-2 inhibitory activity. Molecular docking illustrated that urea moiety formed two critical hydrogen bonds with the DFG residues of VEGFR-2. The results indicated that these biphenyl-aryl ureas could serve as promising lead compounds for further optimization.

Rapid and selective in situ reduction of pyridine- N -oxides with tetrahydroxydiboron

Pyridine-N-oxides are often used as reactive precursors in the syntheses of substituted pyridines. Isolation and subsequent reduction of the associated pyridine-N-oxide intermediates can be challenging. We have discovered that tetrahydroxydiboron functions as a mild, versatile, and remarkably selective reducing agent for pyridine-N-oxides and may be used in an in situ fashion, thus obviating the isolation of N-oxide-containing intermediates. Georg Thieme Verlag Stuttgart New York.

ETHYNYL DERIVATIVES

The present invention relates to ethynyl derivatives of formula I wherein U, V, W, Y, R, R1, R2, R3 and R3′ are as described herein. It has been found that the compounds of general formula I are allosteric modul

ETHYNYL DERIVATIVES AS METABOTROPIC GLUTAMATE RECEPTOR MODULATORS

The present invention relates to ethynyl derivatives of formula I wherein Y is N or CH; with the proviso that Y can only be CH, if at least on of U, V or W are N; U is N or C-R4; V and W are independently N or CH; with the proviso that only one

Rhodium(III)-catalyzed oxidative olefination of pyridines and quinolines: Multigram-scale synthesis of naphthyridinones

A Rh(III)-catalyzed oxidative olefination of pyridines and quinolines has been achieved. This method has a broad substrate scope and has been applied to the expeditious, multigram-scale synthesis of naphthyridinones.

MODULATORS OF CFTR

Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette ("ABC") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator ("CFTR"). The present invention also relates to methods of treating CFTR mediated diseases using compounds of the present invention.

Process for substituted pyridines

This invention relates to processes for preparing compounds of the formula (I) and to processes for preparing certain intermediates of the formula wherein R1is nitro, amino or protected amino; R2is H, fluoro, chloro CF3, n