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 (S)-2-((1H-pyrrolo [2, 3-b] pyridin-5-yl) oxy)-4-(2- (2- (2-cyclopropylphenyl) pyrrolidin-1-yl) -7-azaspiro [3.5] nonan-7-yl) benzoic acid (2.0 g, 3.56 mmol), triethylamine (1.08 g, 10.68 mmol), 2- (7-Azabenzotriazol-1-yl) -N, N, N’, N’-tetramethyluronium hexafluorophosphate (1.62 g, 4.27 mmol) in DCM (100 mL) was stirred for 4 hours at room temperature. Then to the resulting reaction mixture was added 3-nitro-4- (((tetrahydro-2H-pyran-4-yl) methyl) amino) benzenesulfonamide (1.35 g, 4.27 mmol) and DMAP (50 mg, 0.40 mmol). After stirred overnight, the reaction mixture was quenched and washed with NH 4Cl, dried over Na 2SO 4 and concentrated in vacuum. The resulted residue was purified by chromatography column on silica (eluent: PE/EA =1/1, then DCM/MeOH = 60/1 to 40/1), and then the desired compound was obtained (1.3 g, yield: 42.5%). 1H NMR (400 MHz, DMSO-d 6) delta ppm: 11.63 (s, 1H), 11.30 (br, 1H), 8.58 -8.47 (m, 2H), 7.99 (s, 1H), 7.74 (d, J = 8.8 Hz, 1H), 7.55 -7.42 (m, 4H), 7.19 -7.08 (m, 2H), 7.04 -6.90 (m, 2H), 6.66 (d, J = 8.8 Hz, 1H), 6.35 (s, 1H), 6.18 (m, 1H), 4.34 -4.08 (m, 1H), 3.85 (d, J = 8.8 Hz, 2H), 3.31 -3.18 (m, 6H), 3.05 -2.93 (m, 4H), 2.67 -2.51 (m, 1H), 2.35 -2.25 (m, 1H), 2.07 -2.01 (m, 1H), 1.95 -1.68 (m, 6H), 1.62 (d, J = 12.8 Hz, 2H), 1.55 -1.21 (m, 9H), 0.92 -0.85 (m, 2H), 0.65 -0.53 (m, 2H). MS (ESI, m/e) [M+1] + 859.8., 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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