化学合成。
化学合成
合成路线 1(1. 合成:3240-94-6)
产率:74%
合成条件:With thionyl chloride; N,N-dimethyl-formamide In dichloromethane at 0 - 40℃;
实验步骤:在0℃下向搅拌的2-吗啉代乙-1-醇(步骤1,2.5g,13.88mmol,1.0当量)在DCM(25ml)中的溶液中加入亚硫酰氯(5.06mL,69.44mmol,5.0当量),然后 由DMF(Cat。)。 将反应混合物加热至40℃过夜。 在反应完成后(通过TLC监测),将溶剂真空蒸发,得到粗残余物,将其用DCM稀释并用饱和碳酸氢钠溶液洗涤。 在减压下将有机层浓缩,得到粗残余物,将其通过柱色谱法纯化,使用3%MeOH的DCM溶液作为洗脱剂,得到所需化合物(2.0g,收率:74.0%),为无色液体。 1H NMR(DMSO-d6,300MHz):δ3.69(t,J = 6.9Hz,2H),3.57(m,J = 4.5Hz,4H),2.64(t,J = 6.9Hz,2H)和2.43(t) ,J = 4.5Hz,4H); 质量:[M + H] +149.95(10%)。
参考文献:
- [1] Patent: WO2017/149518, 2017, A1. Location in patent: Page/Page column 25; 26 [2] Patent: WO2018/29604, 2018, A1. Location in patent: Page/Page column 47 [3] Journal of the American Chemical Society, 1940, vol. 62, p. 1443,1446 [4] Journal of the American Pharmaceutical Association (1912-1977), 1953, vol. 42, p. 342 [5] Journal of the Indian Chemical Society, 1959, vol. 36, p. 349,352 [6] Journal of the American Chemical Society, 1940, vol. 62, p. 1443,1446 [7] Journal of the American Pharmaceutical Association (1912-1977), 1953, vol. 42, p. 342 [8] Journal of the Indian Chemical Society, 1959, vol. 36, p. 349,352 [9] Journal of the American Chemical Society, 1940, vol. 62, p. 1443,1446 [10] Journal of the American Pharmaceutical Association (1912-1977), 1953, vol. 42, p. 342 [11] Journal of the Indian Chemical Society, 1959, vol. 36, p. 349,352 [12] Journal of Fluorine Chemistry, 1986, vol. 32, p. 41 [13] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 21, p. 6875 - 6884 [14] Tetrahedron, 2016, vol. 72, # 3, p. 420 - 430 [15] Chemical Biology and Drug Design, 2016, vol. 87, # 6, p. 946 - 957 [16] Patent: US2706194, 1951, [17] Patent: US2706194, 1951, [18] Patent: US2706194, 1951,