CN119899197A 一种2-三氟甲基-3-氨基吲哚类化合物及其制备方法

(12)发明专利申请(10)申请公布号CN119899197A(21)申请号202510249837.8A61K31/404(2006.01)有限公司11562(54)发明名称21.一种2-三氟甲基-3-氨基吲哚类化合物，其特征在于，其结构式为9;~72h。3一种2-三氟甲基-3-氨基吲哚类化合物及其制备方法Bioorg.Med.Chem.2011,19,2659-2665;Curr.Pharmaceut.Des.2005,11,1ABCDE4胺衍生物通过β-区域选择性胺化/环化反应，合成3-氨基吲哚类化合物的方法5为起始原料，一锅法合成了2-亚甲基-3-氨基吲哚和2-甲基-3-氨基吲哚类化合物678附图说明[0055]图2为实施例1制备的2-三氟甲基-3-[N-(4-乙氧基[0056]图3为实施例1制备的2-三氟甲基-3-[N-(4-乙氧基[0057]图4为实施例1制备的2-三氟甲基-3-[N-(4-乙氧基[0060]图7为实施例2制备的2-三氟甲基-3-[N-(4-乙基苯基)]氨基-5-乙基吲哚(3b)的[0061]图8为实施例2制备的2-三氟甲基-3-[N-(4-乙基苯基)]氨基-5-乙基吲哚(3b)的9[0063]图10为实施例3制备的2-三氟甲基-3-[N-(4-乙酰氧基苯基)]氨基-5-乙酰氧[0066]图13为实施例4制备的2-三氟甲基-3-[N-(4-氯苯基)]氨基-5-氯吲哚(3d)的[0069]图16为实施例4制备的2-三氟甲基-3-[N-(4-氯苯基)]氨基-5-氯吲哚(3d)的高分二氧基吲哚(3e)的高分辨质谱监测图。isocyanides.Org.Lett.2015,17,14,3490-3493;Radicalperfluoroalkylation-easyaccessto2-perfluoroalkylindol-32.4Hz,1H),6.78-6.69(m,5H),5.28(s,1H),3.97(q,J=6.8Hz,2H),3.90(q,J=7[0090]³c{H}NMR(150MHz,CDCl₃)δ153.6,152.6,139.267.0Hz),124.2,121.2,120.1,117.4(q,Jc-=35.7Hz),116.8,116.3,115.纯化，得到2-三氟甲基-3-[N-(4-乙基苯基)]氨基-5-乙基吲哚(3b),黄色油状液体，24.1mg,产率为48%。[0101]HNMR(400MHz,CDCl₃)88.05(s,1H),7.33(d,J=8.4HJ=8.8Hz,1H),7.03(d,J=8.4Hz,2H),6.70(d,J=8.4Hz,2H),5.39(s,1H),7.6Hz,2H),2.58(q,J=7.6Hz,2H),1.23-1.18(m,6H).[0102]³c{H}NMR(150MHz,CDCl₃)8143.9,136.8,135.0,1Jc-F=266.6Hz),124.3,121.7,119.1,117.5(q,Jc-[0103]19FNMR(376MHz,CDCl₃)δ-58.24.2mg,产率为61%。[0113]HMR(400MHz,DMSO-d₆)812.18(s,1H),7.65(s,1H),7.49(d,J=8.8Hz,1H)7.03(m,2H),6.83(d,J=8.4Hz,2H),6.57(d,J=8.3Hz,2H),2.21(d,J=9.3Hz,6H).[0114]³c{H}NMR(150MHz,DMSO-d₆)8170.11,170.07,145.121.91(q,Jc-F=267.3Hz),124.24,122.46,120[0125]HNMR(400MHz,CDCl₃)88.33(s,1H),7.39-7.29(m,3H),7.146.63(d,J=8.4Hz,2H),5.38(s,1H).[0126]³c{H}NMR(150MHz,CDCl₃)δ144.3,132.7,129.2121.1(q,JC-F=267.3Hz),119.9(q,Jc-F=36.6Hz[0128]HRMS(ESI)成[0137]HNMR(400MHz,CDC₃)88.01(s,1H),1H),6.32(d,J=2.4Hz,1H),6.20(dd,J=8.4,2.4H(s,1H).[0138]³c{H}NMR(150MHz,CDCl₃)8148.2,147.6,143.8,1Jc-F=266.1Hz),121.5,117.9,116.0(q,Jc-F=36.5Hz),108.4,107.2,101.1,100(51.68mg,0.4mmol,2.0equiv.)(59.68mg,0.4mmol,2.0equiv.)3.2mg,产率为9%。(23.24mg,0.2mmol,1.0equiv.)[0174]吲哚骨架本身就具有抗菌、抗炎和抗癌等生物活性；而且文献十6.767十6.767--230220210200190180170160150140130120110100908050364.138310.3919.73230220210200190180170160150140130120110100220313.1512331.1417352333.15729702527364.1712377NL:C19H₂oN₂F₃C19H₂oN₂F₃=333.1573paChrg123学C19HsO4N₂F₃..20.2433.5325.8830.35DeltaDelta294.91973322.95117351.09500373.0993749NL:WENHUANL4-3F#9-下二8882/18页2/18页 T:FTMS+pESIFullloc6Y业230220210200190180170160150140130120110100