Reference of 138891-51-7 ,Some common heterocyclic compound, 138891-51-7, molecular formula is C8H6N2O2, 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.
EXAMPLE 11[2-(6-chloropyridin-3-yl)-4-(2-methoxyethoxy)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)- yl] (imidazo [1,5 -ajpyridin- 1 -yl)methanone (Q-2) O-l (2 g, 6.23 mmol), imidazo[l,5-a]pyridine-l-carboxylic acid (Q-I, 1.112 g,6.86 mmol), EDC (1.315 g, 6.86 mmol), HOBt (0.907 g, 5.92 mmol), and TEA (2.61 mL, 18.70 mmol) were combined in DMF (31 mL) and heated to 60 ºC for 1 hr. Imidazo[l,5-a]pyridine-l- carboxylic acid was prepared according to the literature procedure: Kolar, P.; Petric, A.; Tisler, M.; Felluga, F. J. Heterocycl. Chem. 1991, 7, 1715-1720. The mixture was diluted with EtOAc (100 mL) and washed with sat. aq. NaHCO3 (100 mL), water (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. The resulting residue was purified by gradient elution on silica gel (0 to 45% [10% MeOH in DCM] in DCM over 50 min to afford the title compound as a white solid (2.43 g, 84%). Data for Q-2: 1H NMR (500 MHz, CDCl3) delta 9.35 (s, IH), 8.61 (d, J= 8.3 Hz, IH), 8.26 (d, J= 9.3 Hz, IH), 8.07 (s, IH), 8.01 (d, J= 6.8 Hz, IH), 7.39 (d, J= 8.3 Hz, IH), 7.03 (t, J= 7.8 Hz, IH), 6.76 (t, J= 6.8 Hz, IH), 4.41-5.60 (vbm, 4H), 4.65 (bs, 2H), 3.81 (bs, 2H), 3.46 (s, 3H), 3.13 (bs, 2H); HRMS m/z (M+H) 465.1426 found, 465.1436 required.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,138891-51-7, its application will become more common.
Reference:
Patent; MERCK SHARP &; DOHME CORP.; BRESLIN, Michael, J.; COLEMAN, Paul, J.; COX, Christopher, D.; RAHEEM, Izzat, T.; SCHREIER, John, D.; WO2010/138430; (2010); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem