Electric Literature of 14508-49-7, A common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.
Intermediate 741 ,1 -Dimethylethyl (2-{4-r(2S,4/?)-1 -acetyl-2-methyl-4-(2-pyrazinylamino)-1 , 2,3,4- tetrahvdro-6-quinolinyll-1 /-/-pyrazol-1 -yl)ethyl)methylcarbamateA flask was charged with 2-chloropyrazine (138 mg, 1 .209 mmol) and treated at room temperature under nitrogen with a solution of 1 ,1-dimethylethyl [2-(4-{(2S,4/?)-1 -acetyl-2- methyl-4-amino-1 ,2,3,4-tetrahydro-6-quinolinyl}-1 H-pyrazol-1 -yl)ethyl]methylcarbamate (for a preparation see intermediate 55) (250 mg, 0.605 mmol) in 1 ,4-dioxane (5 mL). 2′- (dicyclohexylphosphino)-N,N-dimethylbiphenyl-2-amine (DavePhos) (47.6 mg, 0.121 mmol), sodium tert-butoxide (1 16 mg, 1 .209 mmol) and tris(dibenzylideneacetone)dipalladium(0) (55.4 mg, 0.060 mmol) were added and the resulting mixture was stirred under nitrogen at 1 10C for 16 h then cooled to room temperature and partitioned between EtOAc (25 mL) and water (25 mL). The layers were separated and the aqueous phase was extracted with EtOAc (25 mL). The combined organic phases were washed with brine (50 mL), dried over Na2S04 and concentrated in vacuo. Purification of this residue on SP4 using a 25 G silica cartridge (gradient: 1 to 5% MeOH in DCM) gave 1 ,1 -dimethylethyl (2-{4-[(2S,4R)-1 -acetyl-2-methyl-4-(2- pyrazinylamino)-1 ,2,3,4-tetrahydro-6-quinolinyl]-1 H-pyrazol-1 -yl}ethyl)methylcarbamate (204.6 mg, 0.344 mmol, 56.9 % yield) as an orange oil.LCMS (Method B): Retention time 0.89 min, [M+H]+ = 506.23
The synthetic route of 14508-49-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GOSMINI, Romain, Luc, Marie; WO2011/54848; (2011); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem