Extracurricular laboratory: Synthetic route of 954-81-4

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 954-81-4 as follows. Formula: C13H14BrNO2

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 954-81-4 as follows. Formula: C13H14BrNO2

Potassium carbonate (0.50 g, 3.6 mmol) was added to a solutionof N-[(4-triphenylmethylamino)butyl]-4-nitrobenzenesulfonamide(0.93 g, 1.8 mmol) and N-(5-bromopentyl)phthalimide(0.54 g, 1.8 mmol) in DMF (12 mL). The mixture was stirred at95 C and monitored by TLC (5% EtOAc in DCM). The reactionwas diluted with ethyl acetate (100 mL) and extracted with water(4 100 mL) and brine (100 mL). The organics were dried oversodium sulfate and concentrated under reduced pressure. The residuewas purified on silica gel (1:3:96 triethylamine/ethyl acetate/dichloromethane) to yield the product as an off-white foam (1.03 g,1.41 mmol, 78%). 1H NMR (500 MHz, DMSO) d 8.35 (d, 2H, J = 9 Hz),8.02 (d, 2H, J = 9 Hz), 7.82 (m, 4H),7.35 (d, 6H, J = 8 Hz), 7.24 (t, 6H,J = 7.5 Hz), 7.13 (t, 3H, J = 7.5 Hz), 3.51 (t, 2H, J = 7 Hz), 3.07 (m, 4H),1.91 (m, 2H), 1.58 (m, 2H), 1.49 (m, 4H), 1.35 (m, 2H), 1.20 (m, 2H);13C NMR (125 MHz, CDCl3) d 168.37, 149.78, 146.04, 145.92,133.95, 132.01, 128.54, 128.16, 127.77, 126.22, 124.32,123.20,70.79, 48.22, 47.98, 42.99, 37.47, 28.08, 27.99, 27.82,26.44, 23.78; HRMS (C42H42N4O6S): calculated 730.2825, observed730.2837

According to the analysis of related databases, 954-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Thomson, Andrew; O’Connor, Sean; Knuckley, Bryan; Causey, Corey P.; Bioorganic and Medicinal Chemistry; vol. 22; 17; (2014); p. 4602 – 4608;,
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