5H-Pyrrolo[2,3-b]pyrazine

Base Information

• Chemical Name: 5H-Pyrrolo[2,3-b]pyrazine
• CAS No.: 4745-93-1
• Molecular Formula: C6H5N3
• Molecular Weight: 119.126
• Hs Code.: 2933990090
• European Community (EC) Number: 830-636-1
• DSSTox Substance ID: DTXSID20963845
• Wikidata: Q27453576
• ChEMBL ID: CHEMBL3628246
• Mol file: 4745-93-1.mol

Synonyms:5H-Pyrrolo[2,3-b]pyrazine;4,7-DIAZAINDOLE;4745-93-1;42430-74-0;1h-pyrrolo[2,3-b]pyrazine;5H-pyrrolo[3,2-b]pyrazine;CHEMBL3628246;MFCD09834819;Pyrrolopyrazine;Pyrrolo(2,3-b)pyrazine;SCHEMBL17198;SCHEMBL17199;SCHEMBL19227644;5H-Pyrrolo[2,3-b]pyrazine #;HFTVJMFWJUFBNO-UHFFFAOYSA-;DTXSID20963845;AMY39470;BDBM50127012;AKOS006326432;CS-W001854;PB29690;(3-Benzyloxyphenyl)hydrazinehydrochloride;DS-10519;SY023099;A7270;BB 0260578;FT-0647134;EN300-98278;A827232;A872888;J-514169;Q27453576;Z1198233190;InChI=1/C6H5N3/c1-2-8-6-5(1)7-3-4-9-6/h1-4H,(H,8,9);36N

Chemical Property of 5H-Pyrrolo[2,3-b]pyrazine

Chemical Property:

• Melting Point: 155-156 °C
• Refractive Index: 1.715
• Boiling Point: 236 °C
• PKA: 11.95±0.20(Predicted)
• Flash Point: 96 °C
• PSA: 41.57000
• Density: 1.349 g/cm³
• LogP: 0.95790
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.048347172
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

98%,99%, ^*data from raw suppliers

5H-Pyrrolo[2,3-b]pyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CNC2=NC=CN=C21
• Uses: 5H-pyrrolo[2,3-b]pyrazine was studied and discovered to be a novel ERK2 inhibitors.

Technology Process of 5H-Pyrrolo[2,3-b]pyrazine

There total 4 articles about 5H-Pyrrolo[2,3-b]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: 59.0%

3-((trimethylsilyl)ethynyl)pyrazine-2-amine → pyrrolo<2,3-b>pyrazine (4745-93-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; for 8h; Reflux; Inert atmosphere;

Reference yield: 42.0%

trimethylsilylacetylene (1066-54-2) + N-(3-chloropyrazin-2-yl)-methanesulfonamide (724442-38-0) → pyrrolo<2,3-b>pyrazine (4745-93-1)

Guidance literature:

With sodium carbonate; lithium chloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In N,N-dimethyl-formamide; at 100 ℃; for 15h;

DOI:10.1016/j.tetlet.2004.08.155

Reference yield:

C7H7N3O2S (1165803-10-0) → pyrrolo<2,3-b>pyrazine (4745-93-1)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; methanol;

DOI:10.1016/j.bmcl.2009.03.110

upstream raw materials:

trimethylsilylacetylene

N-(3-chloropyrazin-2-yl)-methanesulfonamide

C₇H₇N₃O₂S

Downstream raw materials:

C₂₇H₂₅N₃O₅

5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

tert-butyl 7-(1-benzyltriazol-4-yl)pyrrolo[2,3-b]pyrazine-5-carboxylate

Refernces

• 1、 -. "Peptidylarginine deiminase inhibitor and application thereof". Paragraph 0426; 0427; 0431; 0432; 0433. . Retrieved 2019/09/10.
• 2、 Porter, John,Lumb, Simon,Franklin, Richard J.,Gascon-Simorte, Jose M.,Calmiano, Mark,Riche, Kelly Le,Lallemand, Benedicte,Keyaerts, Jean,Edwards, Helen,Maloney, Alison,Delgado, Jean,King, Lloyd,Foley, Anne,Lecomte, Fabien,Reuberson, James,Meier, Christoph,Batchelor, Mark. "Discovery of 4-azaindoles as novel inhibitors of c-Met kinase". scheme or table. p. 2780 - 2784. Retrieved 2009/12/25.