With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1245724-46-2,(S)-Tetrahydro-2H-pyran-3-amine hydrochloride,as a common compound, the synthetic route is as follows.
DIPEA (6.99 mL, 40.00 mmol) was added to ethyl 6-bromo-4-chloroquinoline-3- carboxylate (3.15 g, 10 mmol) and (5)-tetrahydro-2H-pyran-3-amine hydrochloride (1.376 g, 10.00 mmol) in DMA (30 mL) at 25C under air. The resulting solution was stirred at 80C for 16 h. The reaction mixture was diluted with water (100 mL), the precipitate was collected by filtration, washed with water (20 mL) and dissolved into 250 mL EtOAc/DCM (1 : 1). The formed mixture was dried over MgSCM, filtered and evaporated to afford crude (5)-ethyl 6-bromo-4-((tetrahydro-2H-pyran- 3 -yl)amino)quinoline-3 -carboxylate (3.16 g, 83%) as a white solid. The product was used in the next step directly without further purification. NMR Spectrum; 1H NMR (300MHz, DMSO-d6) delta 1.36 (3H, t), 1.70-1.74 (1H, m), 1.75-1.77 (2H, m), 2.03-2.05 (1H, m), 3.58-3.61 (3H, m), 3.80-3.85 (1H, m), 4.01-4.03 (1H, m), 4.35 (2H, q), 7.80 (1H, d), 7.89 (1H, dd), 8.58 (1H, s), 8.67 (1H, d), 8.93 (1H, s). Mass spectrum: m/z: ES+ [M+H]+ 379, 381., 1245724-46-2
As the paragraph descriping shows that 1245724-46-2 is playing an increasingly important role.
Reference£º
Patent; ASTRAZENECA AB; BARLAAM, Bernard, Christophe; PIKE, Kurt, Gordon; HUNT, Thomas, Anthony; (110 pag.)WO2017/153578; (2017); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics