21943-13-5

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromo-3-chloropyrazine is used as a synthetic intermediate for the development of various drug compounds. Its unique molecular structure allows for the creation of new pharmaceuticals with potential therapeutic applications.
Used in Chemical Research:
2-Amino-5-bromo-3-chloropyrazine is used as a reagent in chemical research, particularly in the synthesis and modification of complex molecules. Its reactivity with other compounds makes it a valuable tool in the exploration of new chemical pathways and reactions.
Used in Synthesis of Drug Compounds:
2-Amino-5-bromo-3-chloropyrazine is used as a key component in the synthesis of drug compounds, contributing to the development of new medications with improved efficacy and reduced side effects. Its presence in the molecular structure of these compounds can influence their pharmacological properties and interactions with biological targets.

InChI:InChI=1/C4H3BrClN3/c5-2-1-8-4(7)3(6)9-2/h1H,(H2,7,8)

Upstream product

• 486424-37-7 3-amino-6-bromo-pyrazine-2-carboxylic acid 
• 6863-73-6 3-chloropyrazin-2-amine 

Downstream Products

• 1254328-00-1 3-chloro-5-(3,4,5-trimethoxyphenyl)pyrazin-2-amine 
• 21943-17-9 5-bromo-3-chloropyrazin-2-ol 
• 87444-38-0 5-bromo-3-(methylthio)pyrazin-2-amine 
• 21943-17-9 5-bromo-3-chloropyrazin-2-one 
• 1188409-89-3 3-Chloro-5-[2-methyl-5-(morpholine-4-sulfonyl)-phenyl]-pyrazin-2-ylamine 

Relevant academic research and scientific papers

INDOLE COMPOUNDS AS ANDROGEN RECEPTOR MODULATORS

Provided herein are compounds of formula (V) that bind to BF3 of an androgen receptor (AR), which can modulate the AR for the treatment of Kennedy's disease.

Synthesis method of 2-amino-3, 5-dihalogenated pyrazine

The invention relates to a synthesis method of 2-amino-3, 5-dihalogenated pyrazine, and the synthesis route is shown in the specification. In the formula, X1 is Cl, Br or I; X2 is Cl, Br or I; and X1 and X2 are different, a first halogen source provides X1, and a second halogen source provides X2. The synthesis method disclosed by the invention can be suitable for all types of 2-amino-3, 5-dihalogenated pyrazine except for fluorinated pyrazine. According to the method, the reaction conditions are mild, all reactions can be completed at the temperature of 80 DEG C or below and under the normal pressure condition, and special equipment is not needed; and the method has the advantages of high reaction yield, stable amplification yield, simple post-treatment, economy and convenience.

Selectfluor-promoted regioselective chlorination/bromination of 2-aminopyridines and 2-aminodiazines using LiCl/LiBr

Using LiCl as a chlorine source, the chlorination of 2-aminopyridines or 2-aminodiazines in the presence of Selectfluor and DMF is established under mild conditions. This method gives chlorinated pyridines or diazines in good to high yields with high regioselectivities. Also, this method is extended to the bromination of 2-aminopyridines or 2-aminodiazines by using LiBr. The regioselectivity of the chlorination reaction is strongly dependent upon the substituent pattern in either the 2-aminopyridines or 2-aminodiazines. The synthesis of Buparlisib from chlorinated pyridines was explored. A study of the mechanism revealed that this chlorination occurs via either a pyridine or diazine radical process.

Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library.

Design and synthesis of 2(1H)-pyrazinones as inhibitors of protein kinases

Kinase enzymes play a key role in the development and progression of cancer. Inhibitors of deregulated kinases are effective small molecule anticancer drugs. The 2(1H)-pyrazinone heterocycle is a previously unexploited motif that can fulfil the structural requirements for ATP-competitive inhibition of kinases. Rapid solution-phase syntheses of novel 3,5- and 3,6-disubstituted-2(1H)-pyrazinones were developed through selective, sequential substitution of 2,5-dihalo-3-benzyloxypyrazine and 3,5-dihalo-2(1H)-pyrazinone intermediates. Palladium-catalysed cross-couplings and SNAr reactions were used to introduce substituents chosen on the basis of the calculated physicochemical properties of the target pyrazinones. Representative compounds demonstrated good solubility, kinase inhibitory activity and antiproliferative activity in human tumour cells, confirming the suitability of this chemical class as a kinase-focused library.

Organic compounds

The present invention concerns a compound of formula (I) or a salt, suitably a pharmaceutically acceptable salt, or solvate thereof, wherein the groups R1, R2, Ar′, A and Y are defined in the description, to compositions and use of the compounds in the treatment of inflammatory and allergic conditions.