(1,2,4)Triazolo(1,5-a)pyrazine

Base Information

• Chemical Name: (1,2,4)Triazolo(1,5-a)pyrazine
• CAS No.: 399-66-6
• Molecular Formula: C₅H₄N₄
• Molecular Weight: 120.114
• Hs Code.: 2933990090
• Mol file: 399-66-6.mol

Synonyms:s-Triazolo[1,5-a]pyrazine(8CI)

Chemical Property of (1,2,4)Triazolo(1,5-a)pyrazine

Chemical Property:

• Melting Point: 125-126 °C
• Boiling Point: °Cat760mmHg
• PKA: 0.08±0.30(Predicted)
• Flash Point: °C
• PSA: 43.08000
• Density: 1.48g/cm³
• LogP: 0.12430

Purity/Quality:

97% ^*data from raw suppliers

[1,2,4]Triazolo[1,5-a]pyrazine 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: [1,2,4]Triazolo[1,5-a]pyrazine is a heterocyclic compound that serves as a key scaffold in the development of adenosine A_2A receptor antagonists, which have therapeutic potential for neurological disorders such as Parkinson's disease. Its synthesis involves oxidative cyclization of precursor molecules, highlighting its utility in medicinal chemistry for designing selective and bioactive compounds targeting the A_2A receptor.

Technology Process of (1,2,4)Triazolo(1,5-a)pyrazine

There total 6 articles about (1,2,4)Triazolo(1,5-a)pyrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

N'-hydroxy-N-(pyrazin-2-yl)formimidamide (51519-20-1) → [1,2,4]triazolo[1,5-a]pyrazine (399-66-6)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In tetrahydrofuran; ethyl acetate; at 55 - 60 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.oprd.9b00396

Reference yield: 83.0%

C5H6N4O (51519-20-1) → [1,2,4]triazolo[1,5-a]pyrazine (399-66-6)

Guidance literature:

C₅H₆N₄O; With PPA; at 90 ℃; for 4h;

With sodium hydrogencarbonate; In water; at 0 ℃;

Reference yield: 75.0%

N-hydroxy-N'-pyrazin-2-ylimidoformamide (51519-20-1) → [1,2,4]triazolo[1,5-a]pyrazine (399-66-6)

Guidance literature:

With PPA; at 90 ℃; for 6h;

upstream raw materials:

N-hydroxy-N'-pyrazin-2-ylimidoformamide

N,N-dimethyl-N'-(pyrazin-2-yl)formamidine

C₅H₆N₄O

N'-hydroxy-N-(pyrazin-2-yl)formimidamide

Downstream raw materials:

5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyrazine

(2R,3R)-2-(2,4-difluorophenyl)-3-(5,6-dihydro[1,2,4]triazolo[1,5-a]piperazine-7(8H)-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

(S)-N-(1-([1,2,4]-triazolo[1,5-a]pyrazin-8-yl)pyrrolidin-3-yl)-1-(4-fluorophenyl)-1H-pyrazole-3-carboxamide

8-anilino-1,2,4-triazolo<1,5-a>pyrazine

Refernces

Synthesis of [1,2,4]triazolo[1,5-a]pyrazines as adenosine A_2A receptor antagonists

10.1016/j.bmcl.2005.07.052

The research focuses on the synthesis of [1,2,4]triazolo[1,5-a]pyrazines as potential adenosine A2A receptor antagonists, which are of interest due to their therapeutic potential in treating Parkinson's disease. The purpose of the study was to develop selective A2A antagonists that could improve target affinity, selectivity, and in vivo activity, potentially offering a means to control immunological, cardiovascular, renal, or neurological responses for therapeutic benefit. The researchers synthesized a series of these antagonists using a novel route, starting from 2-amino-3,5-dibromopyrazine (7) and employing oxidative cyclization with reagents such as AlCl3 and Pb(OAc)4 to form the [1,2,4]triazolo[1,5-a]pyrazine nucleus.

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