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

Uses

Used in Pharmaceutical Industry:
2-Amino-3-bromo-5-chloropyrazine is used as a building block for the synthesis of various pharmaceutical drugs. Its unique structure allows for the creation of new drug candidates with potential therapeutic applications.
Used in Organic Chemistry:
In the field of organic chemistry, 2-Amino-3-bromo-5-chloropyrazine serves as a reagent for the preparation of other functionalized pyrazine derivatives. Its versatile chemical properties enable the synthesis of a wide range of compounds with diverse applications.
Due to its specialized nature and potential hazards associated with handling bromine and chlorine-containing compounds, 2-Amino-3-bromo-5-chloropyrazine is typically used by trained professionals in controlled laboratory settings. This ensures safety and the proper execution of chemical reactions and processes.

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

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

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.

Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents

To explore the application potential of dual prodrug strategies in the development of anti-HCV agents, a variety of sofosbuvir derivatives with modifications at the C4 or N3 position of the uracil moiety were designed and synthesized. Some compounds exhibited potent anti-HCV activities, such as 4e and 8a–8c with similar EC50 values (0.20–0.22 μM) comparative to that of sofosbuvir (EC50 = 0.18 μM) in a genotype 1b based replicon Huh-7 cell line. Moreover, 8b displayed a good human plasma stability profile, and was easily metabolized in human liver microsomes expectantly. On the other hand, aiming to discover novel anti-HCV nucleosides, pyrazin-2(1H)-one nucleosides and their phosphoramidate prodrugs were investigated. Several active compounds were discovered, such as 25e (EC50 = 7.3 μM) and S-29b (EC50 = 19.5 μM). This kind of nucleosides were interesting and would open a new avenue for the development of antiviral agents.

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.

COMPOUNDS AND THEIR METHODS OF USE

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 Dravet syndrome or epilepsy 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.

Heterocyclic compounds

The invention concerns pharmaceutically useful compounds of the formula I, in which A1, A2, A3, A4, B1, m, Ar, W, X, Y, Z and R1 have any of the meanings defined herein, and their pharmaceutically acceptable salts, and pharmaceutical compositions containing them. The novel compounds possess endothelin receptor antagonist activity and are useful, for example, in the treatment of diseases or medical conditions in which elevated or abnormal levels of endothelin play a significant causative role. The invention further concerns processes for the manufacture of the novel compounds and the use of the compounds in medical treatment.

New non-peptide endothelin-a receptor antagonists: Synthesis, biological properties, and structure-activity relationships of 5-(dimethylamino)-N- pyridyl-, -N-pyrimidinyl-, -N-pyridazinyl-, and -N-pyrazinyl-1- naphthalenesulfonamides

Use of automated synthesis led to the discovery of several 6-membered nitrogen heterocycles as replacements for the N-isoxazolyl substituent present in the 1-naphthalenesulfonamide endothelin-A (ETA) antagonist 5- (dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulfonamide (BMS 182874). In each of these heterocycles, a small substituent such as halogen para to the position of attachment to the sulfonamide nitrogen atom was found to be advantageous for ETA receptor affinity. Of these heterocycles, 2- pyrazines offered the greatest scope for improving receptor affinity. Optimization of the substituents at the 3- and 5-positions in the pyrazine ring led to potent, ET(A)-selective compounds such as 5-(dimethylamino)-N- (5-chloro-3-methoxy-2-pyrazinyl)-1-naphthalenesulfonamide (7m, ET(A) pIC50 8.1). When dosed orally at 10 mg/kg to conscious, normotensive rats infused with big ET-1, compounds such as 7m showed significant inhibition of the pressor response with a duration of effect lasting for the 5-h course of the experiment.

N-heterocyclic sulfonamides having endothelin receptor activity

The invention concerns pharmaceutically useful compounds of the formula I, in which R 1, R 2, R 3, n, m and Het have any of the meanings defined herein, and their pharmaceutically-acceptable salts, and pharmaceutical compositions containing them. The novel compounds possess endothelin receptor antagonist activity and are useful, for example, in the treatment of diseases or medical conditions in which elevated or abnormal levels of endothelin play a significant causative role. The invention further concerns processess for the manufacture of the novel compounds and the use of the compounds in medical treatment.