Application of 55557-52-3, A common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: Compounds 5-10 (Supplemental Figure 6A, Scheme 1), 12-15 (Supplemental Figure 6B, Scheme 2), and 17, 18 (Supplemental Figure 6C, Scheme 3) were prepared by a modified procedure as reported by Kayser F. et al. (ref 1) and Chen Z. et al. (ref. 2). To a solution of the corresponding thiol, or phenol 4 (0.85 g, 5.0 mmol) in 15 ml DMF (N, N-Dimethylformamide) 3-chloropyrazine-2-carbonitrile (0.66 g, 4.76 mmol) and Na2CO3 (1.01 g, 9.52 mmol), or substituted chrolopyridines, or chlorobenzenes, were added respectively and the resulting mixture was refluxed at 80 C for 12 h. The DMF was evaporated at reduced pressure and the compound A residue was recrystallized from ethyl acetate. The rest of the compounds were purified by flash chromatography on silica gel with ethyl acetate:hexanes (5-100% gradient).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Freeman, Lita A.; Demosky, Stephen J.; Konaklieva, Monika; Kuskovsky, Rostislav; Aponte, Angel; Ossoli, Alice F.; Gordon, Scott M.; Koby, Ross F.; Manthei, Kelly A.; Shen, Min; Vaisman, Boris L.; Shamburek, Robert D.; Jadhav, Ajit; Calabresi, Laura; Gucek, Marjan; Tesmer, John J. G.; Levine, Rodney L.; Remaley, Alan T.; Journal of Pharmacology and Experimental Therapeutics; vol. 362; 2; (2017); p. 306 – 318;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem