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.
Into a 40-mL round-bottom flask, was placed 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i – ylj methyljpiperazin- 1 -yl)-2- [ i4-oxa-2,4, iO-triazatricyclo [7.5 .0.0?[3 ,7j jtetradeca- 1 (9),2,5,7- tetraen-iO-yljbenzoic acid (50 mg, 0.08 mmol, 1 equiv), DCM (3 mL), 3-nitro-4-[[(oxan-4- yl)methyljaminojbenzene-i-sulfonamide (25.2 mg, 0.08 mmol, 1.00 equiv), EDCI (30.6 mg, 0.16 mmol, 2 equiv), DMAP (39.0 mg, 0.32 mmol, 4 equiv). The resulting solution was stirred for overnight at 25 degrees C. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1). The crude product was purified by Flash-Prep-HPLC with the following conditions (IntelFlash-i): Column, Ci8 reversed phase column; mobile phase, Water (1OMMOL/L NH4HCO3+0.05%NH3.H20) and CH3CN (20.0% CH3CN up to 90.0% in 30 mm); Detector, UV 220 nm. This resulted in 19.1 mg (25.90%) of 4-(4- [[2-(4-chlorophenyl)-4,4-dimethylcyclohex- i-en-i -ylj methyljpiperazin- 1 -yl)N-(3-nitro-4-[[(oxan-4-yl)methylj aminojbenzenesulfonyl)-2- [ i4-oxa-2,4, 10- triazatricyclo [7.5 .0.0?[3,7j jtetradeca- 1 (9),2,5,7-tetraen- iO-yljbenzamide as a yellow solid. LCMS: (ES, m/z): M+i=923, R,T= 3.463 mm. The measurements of the retention were done with a reversed phase column (C 18). Shimadzu LCMS 2020; 50*3.0 Agilent Poroshell HPH-Ci8, 2.7um; Eluent A: water (0.05 % ammonia water); Eluent B: Acetonitrile; linear gradient from 5 % acetonitrile to 95 % acetonitrile in 7.0 minutes; Oven temperature 40 C; flow: 1.5 mL/min. ?H NMR (300 MHz, DMSO-d6,ppm) 11.91 (s, iH), 11.26 (s, iH), 8.56 (s, iH), 8.47 (d, J= 2.1 Hz, iH), 7.61 (d, J = 9.0 Hz, iH), 7.48 (d, J = 9.2 Hz, iH), 7.37 (d, J = 8.3 Hz, 2H), 7.20 (s, iH), 7.07 (d, J = 8.3 Hz, 2H), 6.99 – 6.83 (m, 2H), 6.76 (d, J = 29.2 Hz, 2H), 6.14 (s, iH), 4.21 (s, 2H), 3.85 (d, J = 9.3 Hz, 2H), 3.52 (s, 2H), 3.30 – 3.14 (m, 8H), 2.79 (s, iH), 2.23 (d, J = 20.0 Hz, 5H), 1.99 (s, 4H), 1.85 (s, iH), 1.61 (d, J= 11.3 Hz, 2H), 1.42 (s, 2H), 1.25 (s, 2H), 1.03-0.79 (m, 6H). The measurements of the NMR spectra were done with Bruker Avancelli HD300MHz with a probe head of BBOF.
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; NEWAVE PHARMACEUTICAL INC.; CHEN, Yi; LOU, Yan; (108 pag.)WO2019/40550; (2019); A1;,
Tetrahydropyran – Wikipedia
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