With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.65412-03-5,4-(2-Aminoethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
General procedure: Step A: A mixture of 19 TFA salt (9 mg, 0.06 mmol), 11 (32 mg,0.07 mmol) and Cs2CO3 (45 mg, 0.14 mmol) in DMF (0.63 mL)was stirred at 65 C for 12 h. The reaction mixture was filtered,and the crude product was purified by preparative TLC on silicagel eluting with 80% EtOAc/hexanes to give 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-(((hexahydrofuro[2,3-b]furan-3a-yl)methyl)amino)-N-(thiazol-2-yl)benzenesulfonamide (20 mg, 54%)as a white foam. 1H NMR (500 MHz, CDCl3) d 7.77 (d, J = 6.9 Hz,1H), 7.40 (d, J = 3.5 Hz, 1H), 7.23 (d, J = 8.2 Hz, 1H), 6.98 (d,J = 3.5 Hz, 1H), 6.43-6.30 (m, 3H), 5.47 (s, 1H), 5.21 (s, 2H), 5.05-4.95 (m, 1H), 4.09 (dd, J = 8.8, 5.0 Hz, 4H), 3.82-3.70 (m, 7H),3.35 (d, J = 5.2 Hz, 2H), 2.14-1.98 (m, 4H). 584.2 (M+H)+. Step B:A solution of 5-chloro-N-(2,4-dimethoxybenzyl)-2-fluoro-4-(((hexahydrofuro[2,3-b]furan-3a-yl)methyl)amino)-N-(thiazol-2-yl)benzenesulfonamide (20 mg, 0.034 mmol) and TFA (0.05 mL) inDCM (0.34 mL) was stirred at rt for 1 h. The solvents wereremoved, and residue was purified via preparative HPLC (MethodC) to give 4 (6 mg)., 65412-03-5
As the paragraph descriping shows that 65412-03-5 is playing an increasingly important role.
Reference£º
Article; Wu, Yong-Jin; Guernon, Jason; McClure, Andrea; Luo, Guanglin; Rajamani, Ramkumar; Ng, Alicia; Easton, Amy; Newton, Amy; Bourin, Clotilde; Parker, Dawn; Mosure, Kathleen; Barnaby, Omar; Soars, Matthew G.; Knox, Ronald J.; Matchett, Michele; Pieschl, Rick; Herrington, James; Chen, Ping; Sivarao; Bristow, Linda J.; Meanwell, Nicholas A.; Bronson, Joanne; Olson, Richard; Thompson, Lorin A.; Dzierba, Carolyn; Bioorganic and Medicinal Chemistry; vol. 25; 20; (2017); p. 5490 – 5505;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics