Reference of 1480-87-1 ,Some common heterocyclic compound, 1480-87-1, molecular formula is C5H3FN2O2, 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.
To a flask charged with toluene (37.3 mL) were added trans-N-boc- 1 ,4- cyclohexanediamine (2.00 g, 9.33 mmol), potassium carbonate (1.290 g, 9.33 mmol) and 2-fluoro-3-nitropyridine (commercially available from Matrix Scientific, Columbia, SC) (1.326 mL, 9.33 mmol). The resulting bright yellow solution was heated overnight at 120C leading to conversion to the desired product as the primary species along with a more polar impurity according to LC-MS. The mixture was diluted with water, transferred to a separatory funnel and extracted with EtOAc (2x). The combined organic layers were dried with Na2S04, filtered, and dried under reduced pressure providing a bright yellow solid which was triturated with DCM providing tert-butyl ((lr,4r)-4-((3-nitropyridin-2-yl)amino)cyclohexyl)carbamate (1.51 g, 4.49 mmol, 48.1 % yield) as a bright yellow solid. lH NMR (400 MHz, DMSO-d6) delta = 8.49 (dd, J = 1.8, 4.5 Hz, 1 H), 8.41 (dd, J= 1.8, 8.4 Hz, 1 H), 8.06 (d, J= 7.7 Hz, 1 H), 6.79 – 6.69 (m, 2 H), 4.13 – 4.00 (m, J= 3.9, 7.4, 7.4, 1 1.3 Hz, 1 H), 3.29 – 3.20 (m, 1 H), 2.01 – 1.92 (m, 2 H), 1.82 (d, J= 10.6 Hz, 2 H), 1.55 – 1.41 (m, 2 H), 1.38 (s, 9 H), 1.35 – 1.21 (m, 2 H). m/z (ESI) 281.2 (M+H)+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1480-87-1, its application will become more common.
Reference:
Patent; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John, L.; CHAKKA, Nagasree; DIMAURO, Erin; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Hongbing; HUANG, Xin; MARTIN, Matthew, W.; PATEL, Vinod; WO2013/134079; (2013); A1;,
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