With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1350643-72-9,(S)-3-(1-Aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one,as a common compound, the synthetic route is as follows.
Step 1) (S)-3-(1-aminoethyl)-2-phenyl-8-(prop-1-yn-1-yl)isoquinolin-1(2H)-one To a mixture of (S)-3-(1-aminoethyl)-8-chloro-2-phenylisoquinolin-1(2H)-one (1.5 g, 5.0 mmol) (See the synthetic method of step 1-2 of example 8 in WO2015042078) in DMAC (10 mL) was added Cs2CO3 (2.5 g, 7.7 mmol), PdCl2(PCy3)2(0.38 g, 0.51 mmol). The mixture was purged with N2, then propyne (21 mL, 15 mmol, 3-6% in n-heptane) was added, and the mixture was sealed and heated at 110 C. for 5.5 h. Then the mixture was cooled down to room temperature, added EtOAc (150 mL) and water (30 mL). The organic layer was separated and washed with saturated brine (50 mL*5), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc/TEA (v/v/v)=1/10/0.5) to give the title compound as a yellow solid (0.81 g, 53%). MS (ESI, pos.ion) m/z: 303.2 [M+H]+; 1H NMR (600 MHz, CDCl3) delta (ppm): 7.60-7.58 (m, 4H), 7.48 (dd, J=15.3, 7.9 Hz, 2H), 7.42 (d, J=7.7 Hz, 1H), 7.34 (d, J=7.4 Hz, 1H), 6.76 (s, 1H), 3.76-3.70 (m, 1H), 2.13 (s, 3H), 1.30 (d, J=6.5 Hz, 3H). 13C NMR (151 MHz, CDCl3) delta (ppm): 162.5, 138.0, 134.1, 131.6, 129.8, 129.7, 129.4, 129.0, 128.9, 125.6, 125.1, 124.7, 102.3, 92.8, 79.9, 46.9, 23.0, 5.4.
As the paragraph descriping shows that 1350643-72-9 is playing an increasingly important role.
Reference£º
Patent; Sunshine Lake Pharma Co., Ltd.; Calitor Sciences, LLC; Xi, Ning; Wang, Liang; Feng, Xuejin; Liao, Min; (88 pag.)US2019/224197; (2019); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem