1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.
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 (cis-or trans-) 2- ((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(4- (2- (2-chlorophenyl) pyrrolidin-1-yl) cyclohexyl) benzoic acid (142 mg, 0.28 mmol; product of step 6), triethylamine (85 mg, 0.84 mmol), 2- (7-azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (125 mg, 0.33 mmol) in DCM (20 mL) was stirred for 2 hours. To the resulting reaction were added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (104 mg, 0.33 mmol) and DMAP (3 mg, 0.03 mmol) and stirred overnight. The reaction mixture was concentrated in vacuum and purified by chromatography column on silica (eluent: PE/EA = 1/1 to DCM/MeOH = 10/1) to afford a crude product, which was purified with Pre-TLC (DCM/MeOH, 25/1) to give the product Example D1a (17.5 mg, 7.71%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 12.16 (br, 1H), 11.78 (br, 1H), 8.61 (m, 2H), 8.05 (s, 1H), 7.85 (d, J = 8.0 Hz, 1H), 7.63 (s, 1H), 7.55 (m, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.45 (d, J = 8.0 Hz, 1H), 7.27 (d, J = 8.0 Hz, 1H), 7.16 (d, J = 8.0 Hz, 1H), 7.00 (t, J = 8.0 Hz, 1H), 6.94 (d, J = 8.0 Hz, 1H), 6.86 (t, J = 8.0 Hz, 1H), 6.51 (s, 1H), 6.44 (s, 1H), 4.10 (d, J = 8.0 Hz, 1H), 3.85 (d, J = 8.0 Hz, 2H), 3.30-3.23 (m, 5H), 3.16-3.10-3.04 (m, 2H), 2.67-2.55 (m, 1H), 2.42-2.33 (m, 3H), 2.13-1.99 (m, 2H), 1.87-1.82 (m, 2H), 1.67-1.58 (m, 4H), 1.41-1.26 (m, 6H). MS (ESI, m/e) [M+1] + 813.2.
1228779-96-1, 1228779-96-1 3-Nitro-4-(((tetrahydro-2H-pyran-4-yl)methyl)amino)benzenesulfonamide 57474953, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; BEIGENE, LTD.; GUO, Yunhang; XUE, Hai; WANG, Zhiwei; SUN, Hanzi; (493 pag.)WO2019/210828; (2019); A1;,
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