With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.88675-24-5,Tetrahydrofuran-3-amine,as a common compound, the synthetic route is as follows.,88675-24-5
A mixture of (6-(4-((6-chloropyridazin-3-yl)methoxy)-2-oxopyridin-l (2H)-yl)-7,8- dihydronaphthalen-2-yl)methyl methanesulfonate (350 mg, 0.739 mmol), tetrahydrofuran-3- amine (77 mg, 0.886 mmol) and K2CO3 (306 mg, 2.216 mmol) in N, N-dimethylformamide (DMF) (15 mL) was stirred at 80 ¡ãC for 6 hr, then solvent was removed to give the residue which was purified by prep HPLC and chiral prep HPLC to give 4-[(6-chloropyridazin-3- yl)methoxy]-l – {6-[(tetrahydrofuran-3-ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin- 2(lH)-one hydrochloride as a yellow solid (peak 1 , 65 mg, 1 1.2percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 8.05 (d, J = 7.2 Hz, 1H), 7.99 (d, J = 8.8 Hz, 1H), 7.93 (d, J = 8.8 Hz, 1H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.89-6.87 (m, 1H), 6.80 (s, 1H), 6.63 (d, J = 2.4 Hz, 1H), 5.64 (s, 2H), 4.23-4.21 (m, 2H), 4.06-3.95 (m, 3H), 3.86-3.82 (m, 1H), 3.75-3.72 (m, 1H), 3.1 1 -3.09 (m, 2H), 2.76-2.68 (m, 2H), 2.43-2.41 (m, 1H), 2.15-2.10 (m, 1H); ES- LCMS m/z 465 (M+H), and 4-[(6-chloropyridazin-3-yl)methoxy]-l – {6-[(tetrahydrofuran-3- ylamino)methyl]-3,4-dihydronaphthalen-2-yl}pyridin-2(lH)-one hydrochloride as a yellow solid (peak 2, 49.3 mg, 8.5percent yield): 1H NMR (400 MHz, CD3OD) delta ppm 7.98-7.93 (m, 3H), 7.41-7.38 (m, 2H), 7.30-7.28 (m, 1H), 6.85-6.79 (m, 2H), 6.61 -6.60 (m, 1H), 5.64 (s, 2H), 4.23-4.22 (m, 2H), 4.05-4.00 (m, 3H), 3.87-3.83 (m, 1H), 3.73-3.71 (m, 1H), 3.13-3.09 (m, 2H), 2.73-2.67 (m, 2H), 2.41-2.39 (m, 1H), 2.12-2.10 (m, 1H); ES-LCMS m/z 465 ( +H)+. Chiral HPLC method Instrument: Thar 80 Column: AS 250mm*20mm, 20um Mobile phase: A: Supercritical C02, B: MeOH, A: B =55:45 at 80mL/min Column Temp: 38¡ãC Nozzle Pressure: lOOBar Nozzle Temp: 60¡ãC Evaporator Temp: 20¡ãC Trimmer Temp: 25¡ãC Wavelength: 220nm
The synthetic route of 88675-24-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; GLAXOSMITHKLINE LLC; QIN, Donghui; CHRISTENSEN, IV, Siegfried Benjamin; WU, Chengde; ZHANG, Zhiliu; YU, Haiyu; YUAN, Jiangxing; LIN, Xiaojuan; XU, Shanli; LV, Maoyun; YAO, Chen; LI, Lei; HUANG, Xing; GAO, Min; WO2013/166621; (2013); A1;,
Tetrahydrofuran – Wikipedia
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