With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.116131-44-3,3-(Bromomethyl)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
General procedure GP5 (alkylation of hydroxyarylsulfonamides) F G Substituted phenol F (0.20 mmol) was dissolved in dimethyl formamide (3 – 5 mL), cooled in an ice bath and treated with sodium hydride (55% purity, 0.24 mmol, 1.2 eq). After stirring for 20 min the corresponding alkyl or benzyl halide (0.30 mmol, 1.5 eq) was added and the reaction mixture was allowed to warm up and was stirred at room temperature (if not indicated otherwise) until TLC showed consumption of starting material. Water and ethyl acetate were added, the organic phase was washed twice with water, dried and concentrated in vacuo. The crude was purified as indicated in the examples to yield pure Example 165 2-(2-Chlorophenyl)-N-[3-sulfamoyl-4-(tetrahydro-2H-pyran-3- ylmethoxy)phenyl]acetamide According to general procedure GP5, 2-(2-chlorophenyl)-N-(4-hydroxy-3- sulfamoylphenyl)acetamide (102 mg, 0.30 mmol) and 3-(bromomethyl)tetrahydro-2H- pyran (80.6 mg, 0.45 mmol) were converted to 2-(2-Chlorophenyl)-N-[3-sulfamoyl-4- (tetrahydro-2H-pyran-3-ylmethoxy)phenyl]acetamide (stiring overnight at room temperature was followed by stirring at 65 C for 7 h) and was purified by preparative HPLC (Waters XBrigde C185mu 100x30mm, acetonitrile/water + 0.2% aqueous ammonia (32%)) (25 mg, 0.0570 mmol, 19 % yield, 97 % purity). LC-MS (Method B): Rt = 0.98 min MS (ESIneg): m/z = 437 (M-H)+ 1H-NMR (500MHz, DMSO-d6) [ppm]: 1.30 – 1.64 (m, 3H), 1.78 – 1.88 (m, 1H), 2.11 – 2.20 (m, 1H), 3.24 – 3.43 (m, 2H), 3.68 – 3.75 (m, 1H), 3.80 (s, 2H), 3.90 – 4.00 (m, 3H), 6.92 (s, 2H), 7.15 (d, 1H), 7.27 – 7.33 (m, 2H), 7.38 – 7.46 (m, 2H), 7.75 (dd, 1H), 8.01 (d, 1H), 10.28 (s, 1H).
The synthetic route of 116131-44-3 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; WERNER, Stefan; MESCH, Stefanie; BRAeUER, Nico; POOK, Elisabeth; DAHLLOeF, Henrik; NUBBEMEYER, Reinhard; OSMERS, Maren; KALTHOF, Bernd; (386 pag.)WO2016/198374; (2016); A1;,
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