With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.23687-26-5,6-Aminoisoquinoline,as a common compound, the synthetic route is as follows.
K3PO4 (0.544 g, 2.565 mmol), Pd2(dba)3 (0.049 g, 0.0534 mmol) and Xantphos (0.052 g, 0.0891 mmol) were added to a solution of intermediate 13 (0.168 g, 0.891 mmol) in THF (6 mL) while nitrogen was bubbling. After 10 min, isoquinolin-6-amine (0.128 g, 0.891 mmol) was added and the mixture was stirred at rt for 10 min. Then, the mixture was heated at 100 ¡ãC for 16 h. More Pd2(dba)3 (0.049 g, 0.0534 mmol) and Xantphos (0.052 g, 0.0891 mmol) were added under nitrogen flow, and the mixture was heated again at 100 ¡ãC overnight. Pd2(dba)3 (0.049 g, 0.0534 mmol) and Xantphos (0.052 g, 0.0891 mmol) were added were added under nitrogen flow, and the mixture was heated again at 100 ¡ãC for 6 h. The mixture was washed with sat. NaHC03 and extracted with EtOAc. The org layers were dried over MgS04, filtered and the solvent was evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 45/55). The desired fractions were collected and concentrated in vacuo. The product was purified by preparative HPLC (from 75percent [25 mM (0216) NH4HC03] – 25percent [ACN: MeOH 1 : 1] to 0percent [25 mM NH4HC03] – 100percent [ACN: MeOH 1 : 1]). The desired fractions were collected and the solvent was evaporated. The residue was dissolved in DCM and HC1 (5 M in 2-propanol) was added and the resulting mixture was concentrated in vacuo. The residue was triturated with Et20 and filtered to yield compound 7 as an orange solid (0.066 g, 22percent yield). FontWeight=”Bold” FontSize=”10″ H NMR (300 MHz, DMSO-de) delta ppm 1.83 – 2.05 (m, 2 H) 3.17 (br t, J=6.8 Hz, 2 H) 4.58 (dt, J=47.4, 5.8 Hz, 2 H) 5.83 (br s, 1 H) 7.00 (d, J=8.8 Hz, 1 H) 7.12 (dd, J=8.7, 2.7 Hz, 1 H) 7.77 (dd, J=9.2, 1.2 Hz, 1 H) 7.81 (d, J=2.5 Hz, 1 H) 7.99 (d, J=6.9 Hz, 1 H) 8.20 (d, J=9.1 Hz, 1 H) 8.28 (d, J=6.6 Hz, 1 H) 8.42 (s, 1 H) 9.30 (s, 1 H) 10.08 (s, 1 H)
As the paragraph descriping shows that 23687-26-5 is playing an increasingly important role.
Reference£º
Patent; JANSSEN PHARMACEUTICA NV; ANDRES-GIL, Jose, Ignacio; BORMANS, Guy, Maurits, R.; DECLERCQ, Lieven, Denis, Herwig; FIERENS, Katleen; LEENAERTS, Joseph, Elisabeth; MOECHARS, Diederik, Willem, Elisabeth; ROMBOUTS, Frederik, Jan, Rita; KOLB, Hartmuth; ZHANG, Wei; (67 pag.)WO2018/15307; (2018); A1;,
Isoquinoline – Wikipedia
Isoquinoline | C9H7N – PubChem