With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1228779-96-1,3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide,as a common compound, the synthetic route is as follows.
To a solution of 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4- (2-phenylpyrrolidin-1-yl) piperidin-1-yl) benzoic acid (145 mg, 0.3 mmol) in dichloromethane (25 mL) were added o- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (171 mg, 0.45 mmol), triethylamine (1 mL) and 4-dimethylaminopyridine (36 mg, 0.3 mmol). The mixture was stirred for 0.5 h at r.t. Then 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (189 mg, 0.6 mmol) was added. The reaction was continually stirred overnight at r.t. Afterwards, the mixture was washed with water (10 mL) and the organic layers were dried over anhydrous Na 2SO 4 and concentrated. The residue was further purified by prep-HPLC to give the desired product (50 mg, 21.5 %). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 11.68 (m, 2H), 8.58 (d, J = 5.6 Hz, 1H), 8.54 (d, J = 2.4 Hz, 1H), 8.02 (d, J = 2.4 Hz, 1H), 7.77 (d, J = 9.2 Hz, 1H), 7.60-7.40 (m, 5H), 7.33-7.25 (m, 3H), 7.07 (d, J = 9.2 Hz, 1H), 6.68 (d, J = 7.8 Hz, 1H), 6.37 (d, J = 1.5 Hz, 1H), 6.20 (s, 1H), 3.93-3.77 (m, 2H), 3.64 (s, 2H), 3.31-3.20 (m, 6H), 2.59 (s, 3H), 2.28-2.22 (m, 1H), 1.88 (m, 5H), 1.61 (d, J = 12.1Hz, 3H), 1.38 (s, 2H), 1.32-1.16 (m, 3H). MS (ESI, m/e) [M+1] + 780.2.
1228779-96-1, As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.
Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics