Application of 1196152-38-1,Some common heterocyclic compound, 1196152-38-1, name is 2-Bromo-5-(trifluoromethyl)pyrazine, molecular formula is C5H2BrF3N2, 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.
[((1R,4S,6R)-3-{[6-methyl-3-(2-pyrimidinyl)-2-pyridinyl]carbonyl}-3-azabicyclo[4.1.0]hept-4-yl)methyl]amine D25 (80 mg) and 2-bromo-5-(trifluoromethyl)pyrazine (67.4 mg, 0.297 mmol) were dissolved in DMF (2 ml) then sodium carbonate (52.4 mg, 0.495 mmol) was added and the mixture was heated to 50 C. for 2 hours. DMF was evaporated under vacuum and the residue was dissolved in DCM (4 ml) and washed with NaHCO3 saturated solution (4 ml). The organic phase was filtered through a phase separator tube, concentrated under vacuum and the resulting crude product was purified by SCX Chromatography (column size 5 g). Another purification was performed by silica -NH chromatography (Biotage SP-column size 25 g using Cy_EtOAc=5:5 to EtOAc as eluent). It was recovered the title compound E45 (30 mg). UPLC: (Acid Final_QC): rt=0.78 and 0.79 minutes (two rotamers), peaks observed: 470 (M+1). C23H22F3N7O requires 469. 1H NMR (400 MHz, DMSO-d6) delta ppm 8.91-8.82 (m, 2H), 8.36 (d, 1H), 8.20-7.86 (m, 3H), 7.47 (t, 1H), 7.36 (d, 1H) 4.40 (d, 1H), 3.81-3.55 (m, 2H), 3.49-3.35, (m, 2H), 2.38-2.30 (br. s., 3H), 1.80-1.65 (m, 2H), 1.15-1.06 (m, 1H), 1.03-0.91 (m, 1H), 0.80-0.71 (m, 1H), 0.29-0.19 (m, 1H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-5-(trifluoromethyl)pyrazine, its application will become more common.
Reference:
Patent; ALVARO, Giuseppe; Amantini, David; Castiglioni, Emiliano; Di Fabio, Romano; Pavone, Francesca; US2010/144760; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem