6-Chloroimidazo[1,5-A]pyrido[3,2-E]pyrazine

Base Information

• Chemical Name: 6-Chloroimidazo[1,5-A]pyrido[3,2-E]pyrazine
• CAS No.: 240815-50-3
• Molecular Formula: C9H5 Cl N4
• Molecular Weight: 204.619
• DSSTox Substance ID: DTXSID70446431
• Wikidata: Q82265065
• Mol file: 240815-50-3.mol

Synonyms:6-CHLOROIMIDAZO[1,5-A]PYRIDO[3,2-E]PYRAZINE;240815-50-3;SCHEMBL4038518;DTXSID70446431;AB44514;7-chloro-2,4,8,13-tetrazatricyclo[7.4.0.02,6]trideca-1(9),3,5,7,10,12-hexaene

Chemical Property of 6-Chloroimidazo[1,5-A]pyrido[3,2-E]pyrazine

Chemical Property:

• PKA: 1.50±0.50(Predicted)
• PSA: 43.08000
• Density: 1.62±0.1 g/cm3(Predicted)
• LogP: 1.93090
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 204.0202739
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

98%min ^*data from raw suppliers

6-CHLOROIMIDAZO-[1,5-A]PYRIDO-[3,2-E]PYRAZINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC2=C(N=C1)N3C=NC=C3C(=N2)Cl

Technology Process of 6-Chloroimidazo[1,5-A]pyrido[3,2-E]pyrazine

There total 4 articles about 6-Chloroimidazo[1,5-A]pyrido[3,2-E]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: 54.0%

imidazo[1,5-a]-pyrido[2,3-e]pyrazin-6(5H)-one (240815-49-0) → 6-chloroimidazo[1,5-a]pyrido[3,2-e]pyrazine (240815-50-3)

Guidance literature:

With trichlorophosphate; for 12h; Heating;

DOI:10.1021/jm030217e

Reference yield:

2-chloro-3-aminopyridine (6298-19-7) → 6-chloroimidazo[1,5-a]pyrido[3,2-e]pyrazine (240815-50-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium bis(trimethylsilyl)amide / tetrahydrofuran / 1 h / -10 °C

1.2: 40 percent / tetrahydrofuran / 2 h / 20 °C

2.1: 83 percent / potassium carbonate / N,N-dimethyl-acetamide / 6 h / Heating

3.1: 54 percent / phosphorus oxychloride / 12 h / Heating

With sodium hexamethyldisilazane; potassium carbonate; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl acetamide;

DOI:10.1021/jm030217e

Reference yield:

N-(2-chloro-3-pyridinyl)-1H-imidazole-4-carboxamide (240815-48-9) → 6-chloroimidazo[1,5-a]pyrido[3,2-e]pyrazine (240815-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / potassium carbonate / N,N-dimethyl-acetamide / 6 h / Heating

2: 54 percent / phosphorus oxychloride / 12 h / Heating

With potassium carbonate; trichlorophosphate; In N,N-dimethyl acetamide;

DOI:10.1021/jm030217e

upstream raw materials:

imidazo[1,5-a]-pyrido[2,3-e]pyrazin-6(5H)-one

2-chloro-3-aminopyridine

N-(2-chloro-3-pyridinyl)-1H-imidazole-4-carboxamide

Refernces

• 1、 -. "4-AMINO-PYRIDO[3,2-e]PYRAZINES, THEIR USE AS INHIBITORS OF PHOSPHODIESTERASE 10, AND PROCESSES FOR PREPARING THEM". Page/Page column 27. . Retrieved 2008/06/13.
• 2、 Chen, Ping,Doweyko, Arthur M.,Norris, Derek,Gu, Henry H.,Spergel, Steven H.,Das, Jagabundhu,Moquin, Robert V.,Lin, James,Wityak, John,Iwanowicz, Edwin J.,McIntyre, Kim W.,Shuster, David J.,Behnia, Kamelia,Chong, Saeho,De Fex, Henry,Pang, Suhong,Pitt, Sydney,Shen, Ding Ren,Thrall, Sara,Stanley, Paul,Kocy, Octavian R.,Witmer, Mark R.,Kanner, Steven B.,Schieven, Gary L.,Barrish, Joel C.. "Imidazoquinoxaline Src-family kinase p56Lck inhibitors: SAR, QSAR, and the discovery of (S)-N-(2-chloro-6-methylphenyl)-2-(3-methyl-1- piperazinyl)imidazo-[1,5-a]pyrido[3,2-e]pyrazin-6-amine (BMS-279700) as a potent and orally active inhibitor with excellent in vivo antiinflammatory activity". . p. 4517 - 4529. Retrieved 2007/10/03.