With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.59669-59-9,3-(tert-Butyl)isoxazol-5-amine,as a common compound, the synthetic route is as follows.
59669-59-9, Step 6: Synthesis of compound B-7Activation of 55.9 g (22.3 mmol) of compound B-6 is achieved by treatment with thionyl chloride (600 mL) at 60 ¡ãC for 3 h. The reaction mixture is cooled to room temperature and excess thionyl chloride is removed under reduced pressure.The crude acid chloride is dissolved in DCM (400 mL) and added to a solution of 31.3 g (22.3 mmol) of 3-tert-Butyl-isoxazol-5-ylamine and N,N-diisopropylethylamine (194 mL) in DCM (250mL). The reaction is stirred at room temperature for 16 h. The reaction mixture is diluted with DCM (1350 mL) and washed with saturated aqueous NaHCC>3 solution (1000 mL). The organic layer is dried over Na2S04, filtered and the filtrate is concentrated under reduced pressure. The crude product is purified by dry-flash column chromatography (2 kg silica, eluent: DCM, 0-20percent ethyl acetate). The resulting solid is recrystallised from isopropanol/heptanes (1/1. 2 L), then dried under reduced pressure to afford 80 g of compound B-7 as an off-white powder. Yield 96percent; ES-MS: m/z 373 [M+H]; XH NMR (360 MHz, CHLOROFORM-d) delta ppm 1.35 (9 H, s), 1.41 – 1.55 (2 H, m), 1.74 (6 H, s), 1.82 – 1.91 (2 H, m), 2.29 – 2.52 (1 H, m), 2.92 (2 H, d, 7=6.58 Hz), 3.34 – 3.49 (2 H, m), 3.88 – 4.00 (2 H, m), 6.30 (1 H, s), 9.38 (1 H, s).
As the paragraph descriping shows that 59669-59-9 is playing an increasingly important role.
Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HICKEY, Eugene Richard; RIETHER, Doris; ERMANN, Monika; WO2012/12307; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem