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.
Into a 8- mL round-bottom flask, was placed 4-(4-[[2-(4-chlorophenyl)-4,4-dimethylcyclohex-l-en-l- yl]methyl]piperazin-l-yl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca-l(9),2,5,7- tetraen-lO-yl]benzoic acid (30 mg, 0.05 mmol, 1 equiv), 3-nitro-4-[[(oxan-4- yl)methyl]amino]benzene-l-sulfonamide (17 mg, 0.06 mmol, 1.20 equiv), EDCI (18 mg, 0.09 mmol, 2 equiv), DMAP (23 mg, 0.19 mmol, 4 equiv), DCM (3 mL). The resulting solution was stirred for overnight at room temperature. The resulting mixture was concentrated. The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-l): Column, C18 silica gel; mobile phase, Water(0. l%FA) and ACN (48.0% ACN up to 53.0% in 7 min, hold 95.0% in 1 min, down to 48.0% in 1 min within 5 ; Detector, UV 254 nm. This resulted in 10.6 mg (24.15%) of 4-(4-[[2-(4-chlorophenyl)-4,4- dimethylcyclohex- l-en- l-yl]methyl]piperazin- l-yl)-N-(3-nitro-4-[[(oxan-4- yl)methyl]amino]benzenesulfonyl)-2-[l4-thia-2,4,l0-triazatricyclo[7.5.0.0A[3,7]]tetradeca- l(9),2,5,7-tetraen-l0-yl]benzamide as a yellow solid. LC-MS: (ES, m/z ): M+l=939, R,T= 3.55 min. The measurements of the retention were done with a reversed phase column (C18). Shimadzu LCMS 2020; 50*3.0 Kinetex 2.6u XB-C18 , 2.6 microm; Eluent A: water (0.05 % TFA); Eluent B: Acetonitrile; linear gradient. H-NMR: (CDC13, 300 ppm): 8.7l(s, 1H), 8.49 (s, 1H), 7.99-7.97(m, 1H), 7.8l-7.77(m, 1H), 7.38-7.28(m, 4H), 7.0l-6.93(m, 2H), 6.88- 6.72(m, 3H), 3.36(s, 1H), 4.06-3.26(m, 18H), 2.73-2.22(m, 6H), 2. l3-l.73(m, 3H), 1.79- l.25(m, 6H), l.00(s, 6H).
As the paragraph descriping shows that 1228779-96-1 is playing an increasingly important role.
Reference£º
Patent; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; (475 pag.)WO2020/41406; (2020); A1;,
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