Downstream synthetic route of 14441-90-8

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

14441-90-8, 5-Phenylisoxazole-3-carboxylic acid is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step-4: N-(2-(5-(methoxymethyl)-1,3,4-thiadiazol-2-yl)ethyl)-5-phenylisoxazole-3-carboxamide To an ice-cooled suspension of 5-phenyl-isoxazole-3-carboxylic acid (2.08 g, 0.011 mol) in DCM (40 mL) was slowly added T3P solution (10.5 mL, 0.016 mol, 50% solution in EtOAc) followed by addition of triethylamine (2.23 g, 0.022 mol) and solution of 2-(5-methoxymethyl-[1,3,4]thiadiazol-2-yl)-ethylamine (1.88 g, ca. 0.011 mol) in DCM (10 mL). The reaction mixture was stirred at room temperature for 18 h and quenched onto ice-water (150 mL). Separated DCM layer was washed with saturated NaHCO3 solution (3*75 mL), water (2*50 mL) and brine (100 mL). Organic layer was dried over anhydrous Na2SO4 and concentrated under vacuum to obtained crude solid product. The crude solid was triturated in diethyl ether (50 mL), filtered and dried to afford desired product. Yield: 48%; Appearance: off-whites solid Analytical data: 1H NMR (400 MHz, CDCl3): delta 7.79-7.76 (m, 2H), 7.50-7.46 (m, 3H), 7.41 (br, 1H), 6.93 (s, 1H), 4.82 (s, 2H), 3.99-3.94 (m, 2H), 3.45 (s, 3H), 3.42-3.41 (m, 2H). LC-MS: (M+H)+ 345.0; HPLC Purity: 99.87% at 254 nm & 99.32% at 220 nm.

14441-90-8, As the paragraph descriping shows that 14441-90-8 is playing an increasingly important role.

Reference£º
Patent; PROTEOSTASIS TEHRAPEUTICS, INC.; Bastos, Cecilia M.; Munoz, Benito; Tait, Bradley; (48 pag.)US2017/1993; (2017); A1;,
Isoxazole – Wikipedia
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