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.
The mixture of 3- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy) -4′- (2- (2-cyclopropylphenyl) pyrrolidin-1-yl) -2′, 3′, 4′, 5′-tetrahydro- [1, 1′-biphenyl] -4-carboxylic acid (700 mg, 1.34 mmol), triethylamine (106 mg, 4.05 mmol), 2- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (616 mg, 1.62 mmol) in DCM (10 mL) was stirred for 2 hours at room temperature. To the reaction mixture was added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (512 mg, 1.62 mmol) and DMAP (17 mg, 0.14 mmol) and stirred overnight. The reaction mixture was washed with brine, dried over Na 2SO 4 and concentrated in vacuo, then purified by chromatography column on silica (eluent: DCM/MeOH = 50/1 to 15/1) to afford a crude product (490 mg). The crude product was purified with Pre-HPLC to give the product (1.65 mg, 1.26%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.25 (br, 1H), 11.68 (br, 1H), 8.51 (m, 2H), 7.99 (s, 1H), 7.79 (d, J = 12.0 Hz, 1H), 7.61-7.47 (m, 4H), 7.28-7.07 (m, 5H), 6.73 (s, 1H), 6.37 (s, 1H), 5.99-5.85 (m, 1H), 5.32-5.28 (m, 1H), 3.85 (d, J = 8.0 Hz, 2H), 3.75-3.51 (m, 2H), 3.22 (m, 5H), 2.42-1.97 (m, 8H), 1.86 (s, 2H), 1.73 (s, 1H), 1.61-1.57 (m, 2H), 1.45-1.37 (m, 1H), 1.23 (m, 2H), 1.07-0.93 (m, 2H), 0.71-0.59 (m, 2H). MS (ESI, m/e) [M+1] + 817.2.
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;,
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