875781-41-2

Usage

Uses

Used in Pharmaceutical Synthesis:
5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine is used as a key intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into the molecular structures of various drugs. Its unique functional groups facilitate the creation of new compounds with potential therapeutic effects.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine is utilized as a building block for the synthesis of complex organic compounds. Its reactivity and structural features make it suitable for the development of novel organic materials with specific properties.
Used in Medicinal Chemistry Research:
5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine is employed as a research tool in medicinal chemistry to explore its potential as a precursor for the development of new drugs. Its synthetic versatility allows for the modification and optimization of its structure to enhance pharmacological activity.
Used in Drug Discovery Programs:
In drug discovery, 5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine is used as a starting material for the design and synthesis of new drug candidates. Its unique structural features and potential pharmacological properties make it a promising candidate for the development of innovative therapeutic agents.
Used in Chemical Reactivity Studies:
5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-amine is also used in studies focused on understanding the reactivity of chemical compounds. The presence of the trimethylsilyl group and its steric hindrance effects on the molecule's interactions with other compounds provide valuable insights into the factors influencing chemical reactivity.

Upstream product

• 24241-18-7 2-amino-3,5-dibromopyrazine 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1201186-54-0 2-bromo-5-(p-toluenesulfonyl)-5H-pyrrolo[2,3-b]pyrazine 
• 1232423-55-0 tert-butyl N-(5-bromo-3-ethynyl-pyrazin-2-yl)-N-tert-butoxycarbonyl-carbamate 
• 1349734-86-6 di-tert-butyl (5-bromo-3-(3-(4-(chloromethyl)phenyl)isoxazol-5-yl)pyrazin-2-yl)carbamate 
• 1349734-89-9 di-tert-butyl (5-bromo-3-(3-(4-(bromomethyl)phenyl)isoxazol-5-yl)pyrazin-2-yl)carbamate 
• 1349734-88-8 tert-butyl N-[5-bromo-3-[3-(p-tolyl)isoxazol-5-yl]pyrazin-2-yl]-N-tert-butoxycarbonylcarbamate 
• 1349734-93-5 tert-butyl N-[[4-[5-[3-[bis(tert-butoxycarbonyl)amino]-6-bromopyrazin-2-yl]isoxazol-3-yl]phenyl]methyl]-N-cyclopropylcarbamate 
• 1349734-90-2 di-tert-butyl (5-bromo-3-(3-(4-((isopropylamino)methyl)phenyl)isoxazol-5-yl)pyrazin-2-yl)carbamate 
• 1349734-98-0 1-((4-(5-(3-amino-6-bromopyrazin-2-yl)isoxazol-3-yl)benzyl)amino)-2-methylpropan-2-ol 
• 1349734-97-9 5-bromo-3-(3-(4-(chloromethyl)phenyl)isoxazol-5-yl)pyrazin-2-amine 
• 875781-43-4 2-bromo-5H-pyrrolo[2,3-b]pyrazine 
• 875781-44-5 2-bromo-7-iodo-5H-pyrrolo[3,2-b]pyrazine 
• 875781-45-6 2-bromo-7-iodo-5-tosyl-5H-pyrrolo[3,2-b]pyrazine 
• 1229583-75-8 2-bromo-7-(1H-indol-5-yl)-5-tosyl-5H-pyrrolo[3,2-b]pyrazine 
• 1229582-37-9 7-(1H-indol-5-yl)-2-(3,4,5-trimethoxyphenyl)-5H-pyrrolo[3,2-b]pyrazine 

Relevant academic research and scientific papers

Development of a Scalable Enantioselective Synthesis of JAK Inhibitor Upadacitinib

Process development of a six-stage synthesis of upadacitinib, a JAK1 inhibitor, is described. It is highlighted by an enantioselective and diastereoselective hydrogenation of a tetrasubstituted olefin to set the two pyrrolidine stereocenters. Preparation of the main fragments and strategies to link them together, optimization of the imidazole cyclization, and in-depth understanding of the formation of the urea moiety at the final stage are discussed.

Synthetic method of indole or azabenzopyrrole compound

The invention relates to a synthetic method of an indole or azabenzopyrrole compound. The synthetic method comprises the following steps: carrying out cyclization reaction on a compound A and disubstituted amine in a solvent, wherein the structural general formula of the disubstituted amine is NH(R2)2, R2 is respectively and independently selected from C1-C6 alkyl, C1-C6 alkyl hydroxyl, C1-C6 alkyl O-C1-C6 alkyl, C1-C6 alkyl NH-C1-C6 alkyl or C1-C6 alkylamino, and the two R2 are connected with each other to form a ring or not form a ring. According to the synthetic method of the indole or azabenzopyrrole compound, the disubstituted amine compound with a specific structural general formula and the terminal alkynyl of the intermediate are subjected to an addition reaction, the rigid structure of the terminal alkynyl is changed, and the structure of alkenyl amine is changed, so that under mild reaction conditions, ring closing of pyrrole groups in indole or azabenzopyrrole compounds is realized, side reactions are few, the product yield is high, and the production cost of the product is reduced from the source.

Discovery and Toxicological Profiling of Aminopyridines as Orally Bioavailable Selective Inhibitors of PI3-Kinase γ

Using a novel physiologically relevant in vitro human whole blood neutrophil shape change assay, an aminopyrazine series of selective PI3Kγinhibitors was identified and prioritized for further optimization. Severe solubility limitations associated with the series leading to low oral bioavailability and poor exposures, especially at higher doses, were overcome by moving to an aminopyridine core. Compound 33, with the optimal balance of on-target activity, selectivity, and pharmacokinetic parameters, progressed into in vivo studies and demonstrated good efficacy (10 mg/kg) in a rat model of airway inflammation. Sufficient exposures were achieved at high doses to support toxicological studies, where unexpected inflammatory cell infiltrates in cardiovascular tissue prevented further compound development.

PYRROLIDINE COMPOUNDS, ITS SALT AND USE IN THE PREPARATION OF UPADACITINIB THEREOF

The present invention relates to process for the preparation of a pyrrolidine compounds useful as key intermediate for the preparation of upadacitinib. More specifically the present invention relates to a process for preparing compound of Formula I, or pharmaceutically acceptable salts, polymorphs, isomers thereof. The present invention further provides a process for the preparation of upadacitinib using compounds of Formula I. Moreover, the present invention provides various crystalline solvates and crystalline hydrates of Upadacitinib or its pharmaceutically acceptable salts thereof.

Influenza virus replication inhibitors and uses thereof (by machine translation)

The invention provides a compound as an influenza virus replication inhibitor, a method for preparing the same, a pharmaceutical composition containing the compound and application. (by machine translation)

Synthesis and Structure-Activity Relationships of 3,5-Disubstituted-pyrrolo[2,3- b]pyridines as Inhibitors of Adaptor-Associated Kinase 1 with Antiviral Activity

There are currently no approved drugs for the treatment of emerging viral infections, such as dengue and Ebola. Adaptor-associated kinase 1 (AAK1) is a cellular serine-threonine protein kinase that functions as a key regulator of the clathrin-associated host adaptor proteins and regulates the intracellular trafficking of multiple unrelated RNA viruses. Moreover, AAK1 is overexpressed specifically in dengue virus-infected but not bystander cells. Because AAK1 is a promising antiviral drug target, we have embarked on an optimization campaign of a previously identified 7-azaindole analogue, yielding novel pyrrolo[2,3-b]pyridines with high AAK1 affinity. The optimized compounds demonstrate improved activity against dengue virus both in vitro and in human primary dendritic cells and the unrelated Ebola virus. These findings demonstrate that targeting cellular AAK1 may represent a promising broad-spectrum antiviral strategy.

JAK kinase inhibitor, preparation method thereof, and application in the field of medicines

The application relates to a JAK kinase inhibitor, a preparation method thereof, and an application in the field of medicines and belongs to the field of medical chemistry. In the application, a series of novel small-molecular JAK inhibitors are provided and are represented as the general formula (II). The compounds have better effects and higher safety in prevention or treatment on JAK-related adaptation diseases.

INHIBITORS OF INFLUENZA VIRUS REPLICATION AND USES THEREOF

The invention provides a class of compounds as inhibitors of influenza virus replication, preparation methods thereof, pharmaceutical compositions containing these compounds, and uses of these compounds and pharmaceutical compositions thereof in the treatment of influenza.

Upadacitinib tartrate: Tyrosine-protein kinase JAK1 inhibitor Treatment of autoimmune inflammatory diseases Treatment of rheumatoid arthritis

Upadacitinib tartrate (ABT-494) is a potent and selective tyrosine-protein kinase JAK1 inhibitor being developed for the treatment of systemic autoimmune inflammatory diseases, including rheumatoid arthritis (RA), Crohn's disease, ulcerative colitis and psoriatic arthritis. In vitro, upadacitinib demonstrated higher selectivity for inhibiting JAK1 over JAK2 and JAK3, suggesting a potentially improved therapeutic profile in treating patients with inflammatory diseases compared to nonselective JAK inhibitors. Upadacitinib has demonstrated safety and efficacy in phase II trials in patients with RA and inflammatory bowel disease, and is currently in phase III development for these indications.

Heteroaromatic compound and application thereof to drug

The invention discloses a heteroaromatic compound and application thereof to drug. In particular, the invention provides a heteroaromatic compound or stereoisomers thereof, geometric isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites, pharmaceutically acceptable salts or prodrugs thereof, and a pharmaceutical composition comprising the compound provided by the invention. The invention also discloses application of the compound provided by the invention or the pharmaceutical composition thereofto preparation of a medicine for reatment of autoimmune diseases or proliferative diseases.