Reference of 1018505-59-3 ,Some common heterocyclic compound, 1018505-59-3, molecular formula is C11H18N4, 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 solution of 3-chloro-7-(3, 5-dimethoxyphenyl) isoqinoline (50 mg, 0.167 mmol) , 5-(4- ethylpiprazine-l-yl) pyridine-2-amine (38 mg , 0.183 mmol), X-Phos ( 8 mg, 10 mol% ) and cesium carbonate (108.4 mg, 0.334 mmol) in Toluene (4 mL) and t-BuOH (1 mL) (4: 1) argon was purged for 20 min. Then was added Pd(OAc)2 (3.76 mg, 10 mol%) again argon was purged for 5 min. The reaction mixture was heated at 120C for O/N. The reaction mixture was cooled to room temperature and filtered through celite pad and filtrate was concentrated under reduced pressure. Product was purified by column chromatography on silica gel column using DCM: MeOH: NH3 aq. (94:6: 1%) as an eluent to afford 7-(3,5-dimethoxyphenyl)-N-[5- (4-ethylpiperazin-l-yl)pyridin-2-yl]isoquinolin-3 -amine (20 mg) as a brown solid. 1H NMR (400 MHz, CDC13) delta 9.00 (s, 1H), 8.14 (s, 1H), 8.06 (d, J = 2.5 Hz, 1H), 8.00 (s, 1H), 7.79 (dd, J = 19.3, 8.6 Hz, 2H), 7.42 (s, 1H), 7.31 (dd, J = 8.9, 2.7 Hz, 1H), 7.10 (d, J = 8.9 Hz, 1H), 6.83 (d, J = 1.9 Hz, 2H), 6.49 (s, 1H), 3.88 (s, 6H), 3.25 – 3.14 (m, 4H), 2.66 (d, J = 4.4 Hz, 4H), 2.50 (q, J = 7.1 Hz, 2H), 1.15 (t, J = 7.2 Hz, 3H).M/Z: 469.58, M+l : 470.4, tR= 2.1 min. (System 2)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1018505-59-3, its application will become more common.
Reference:
Patent; EVOTEC (UK) LTD.; MC CARTHY, Clive; MILLS, Matthew; WO2014/44846; (2014); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem