76537-18-3

Basic information

• Product Name: 2-AMINO-3-BROMO-5-CHLOROPYRAZINE
• Synonyms: 3-Bromo-5-chloropyrazin-2-ylamine;2-AMINO-3-BROMO-5-CHLOROPYRAZINE;2-Pyrazinamine, 3-bromo-5-chloro-;3-broMo-5-chloropyrazin-2-aMine;3-Bromo-5-chloro-2-aminopyrazine
• CAS NO: 76537-18-3
• Molecular Formula: C₄H₃BrClN₃
• Molecular Weight: 208.45
• Mol File: 76537-18-3.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 298.417 °C at 760 mmHg
• Flash Point: 134.278 °C
• Appearance: /
• Density: 1.96
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 0.89±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-3-BROMO-5-CHLOROPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-3-BROMO-5-CHLOROPYRAZINE(76537-18-3)
• EPA Substance Registry System: 2-AMINO-3-BROMO-5-CHLOROPYRAZINE(76537-18-3)

Safety Data

• Hazardous Substances Data: 76537-18-3(Hazardous Substances Data)

Usage

General Description

2-Amino-3-bromo-5-chloropyrazine is a chemical compound with the formula C4H4BrClN3. It is a pyrazine derivative that contains a bromine atom, a chlorine atom, and an amino group attached to a five-membered ring. 2-Amino-3-bromo-5-chloropyrazine has potential applications in the pharmaceutical industry as a building block for the synthesis of various pharmaceutical drugs. It is also used in the field of organic chemistry as a reagent for the preparation of other functionalized pyrazine derivatives. Its unique structure and properties make it a valuable intermediate for the development of new chemical compounds and materials. Due to its specialized nature, 2-Amino-3-bromo-5-chloropyrazine is typically used by trained professionals in laboratory settings.

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

Upstream product

• 33332-29-5 2-amino-5-chloropyrazine 

Downstream Products

• 84066-11-5 3-methyl-6-chloro-8-bromoimidazo<1,2-a>pyrazine 
• 874-31-7 2-amino-5-chloro-3-methoxypyrazine 
• 1364266-97-6 (+/-)-methyl 4-(3-amino-6-chloropyrazin-2-yl)-2-(1-(2-(trifluoromethyl)phenyl)ethoxy)benzoate 
• 1244776-64-4 5-chloro-3-((trimethylsilyl)ethynyl)pyrazine-2-amine 
• 17231-50-4 6-chloro-3-aminopyrazine-2-carbonitrile 

Relevant articles and documents

The complete synthesis of favipiravir from 2-aminopyrazine

Favipiravir was first synthesized from an inexpensive and commercially available starting material, 2-aminopyrazine. The preferred route embedded within Scheme?4 consisted of seven steps, and was highlighted by the novel and efficient synthesis of 3,6-dichloropyrazine-2-carbonitrile 8. This intermediate was prepared in four successive steps which were regioselective chlorination of the pyrazine ring, bromination, Pd-catalyzed cyanation, and Sandmeyer diazotization/chlorination. This protocol eliminated the hazardous POCl3 of previous synthetic methods and offered a better yield (48%) which was 1.3-fold higher than a recently published procedure. From intermediate 8, the subsequent nucleophilic fluorination, nitrile hydration and hydroxyl substitution efficiently afforded the target product. Another synthetic approach with the same starting material was also investigated to bypass the allergy-causing dichloro intermediate 8. However, the key step of monofluorination at the pyrazine C6 position of intermediate 19 or 22 was not achieved.

ION CHANNEL MODULATORS

The present invention is directed to, in part, fused heteroaryl compounds and compositions useful for preventing and/or treating a disease or condition relating to aberrant function of a voltage-gated, sodium ion channel, for example, abnormal late/persistent sodium current. Methods of treating a disease or condition relating to aberrant function of a sodium ion channel including neurological disorders (e.g., Dravet syndrome, epilepsy), pain, and neuromuscular disorders are also provided herein.

PYRROLOPYRAZINES AND PYRAZOLOPYRAZINES USEFUL AS INHIBITORS OF PROTEIN KINASES

The present invention relates to compounds of formula (I): wherein x, R1, R2 and R3 denote as in Claim 1, useful as inhibitors of Aurora protein kinase. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of usig the compositions in the treatment of various disease, conditions, or disorders. The invention also provides processes for preparing compounds of the inventions.