13958-99-1

Basic information

• Product Name: 3-Bromopyridine-4-carboxamide
• Synonyms: 3-Bromopyridine-4-carboxamide;3-Bromoisonicotinamide;3-broMo-2-carbaMoylpyridine-4-carboxylic acid;3-Bromo-4-pyridinecarboxamide;Isonicotinamide, 3-bromo-
• CAS NO: 13958-99-1
• Molecular Formula: C₆H₅BrN₂O
• Molecular Weight: 201.0207
• EINECS: 251-156-6
• Product Categories: Pyridines
• Mol File: 13958-99-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 316.252 °C at 760 mmHg
• Flash Point: 145.064 °C
• Appearance: /
• Density: 1.710±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3-Bromopyridine-4-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromopyridine-4-carboxamide(13958-99-1)
• EPA Substance Registry System: 3-Bromopyridine-4-carboxamide(13958-99-1)

Safety Data

• Hazardous Substances Data: 13958-99-1(Hazardous Substances Data)

Usage

General Description

3-Bromopyridine-4-carboxamide is a chemical compound with the molecular formula C6H5BrN2O. It belongs to the class of organic compounds known as pyridine and derivatives, which are compounds containing a pyridine ring, a six-membered aromatic heterocycle which consists of one nitrogen atom and five carbon atoms. The chemical appears as a crystal white solid and it is widely used in the field of chemistry for various applications, such as in chemical synthesis and as a building block in organic synthesis. It is relatively stable, however, it may produce hazardous decomposition products if it comes into contact with heat or flames.

InChI:InChI=1/C6H5BrN2O/c7-5-3-9-2-1-4(5)6(8)10/h1-3H,(H2,8,10)

Upstream product

• 626-55-1 3-Bromopyridine 
• 541-41-3 chloroformic acid ethyl ester 
• 13959-02-9 3-bromoisonicotinic acid 

Downstream Products

• 118160-00-2 4-cyano-3-(phenylethynyl)pyridine 
• 16081-85-9 2-phenylpyrido[3,4-d]pyrimidin-4(3H)-one 
• 1613436-00-2 3-(4-methylphenyl)-2,6-naphthyridin-1-one 
• 1613435-99-6 4-cyano-3-(4-methylphenylethynyl)pyridine 
• 1373686-80-6 N-(3-(1-amino-3-methyl-3,4-dihydro-2,6-naphthyridin-3-yl)-4-fluorophenyl)-5-cyanopicolinamide 
• 1373687-50-3 tert-butyl (3-(5-(5-cyanopicolinamido)-2-fluorophenyl)-3-methyl-3,4-dihydro-2,6-naphthyridin-1-yl)carbamate 

Relevant articles and documents

Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases

Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.

A facile synthesis of 3-amino-1(2)H-pyrazolo[3,4-c]pyridine

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