一种氨基甲酰尿嘧啶衍生物及其应用_3

文档序号:9742271阅读:来源:国知局
实施例3.化合物2.2的合成
[0062] 如实施例1所述方法,制备得化合物2.2,表征数据如下:IR(f ilm)vmax: 3079,2914, 2844,1750,1700,1570,1486,1387(^5? 匪R(400MHz,CDC13)S0.89(t,J = 6.8Hz,3H), 1.29-1.38(m,6H),1.59-1.62(m,2H),1.99(d,J=1.2Hz,3H),3.35-3.40(m,2H),8.24(q,J =1.2Hz,lH),8.60(s,lH),9.09(br,lH)ppm;13C 匪R(100MHz,CDC13)S12.4,14.0,22.5, 26.5,29.2,31.4,41.2,112.3,134.6,150.0,151.5,163.0ppm;MS(ESI,m/z):252(M-H)-; Anal.calcd for C12H19N3O3:C,56.90;H,7.56;N,16.59;Found:C,57.08;H,7.55;N,17.02.
[0063] 实施例4.化合物2.3的合成
[0064] 如实施例1所述方法,制备得化合物2.3,表征数据如下:4 NMR(400MHz,⑶Cl3)δ 0.88(t ,J = 6.8Hz,3H),1.17(t ,J = 7.6Hz,3H), 1.32-1.37(m,6H), 1.57-1.62(m,2H), 2.43 (q ,J = 7.2Hz,2H) ,3.37-3.42(m,2H) ,8.24(s, 1H) ,9.21 (br, 1H), 10.21 (s , lH)ppm; 13C NMR (100MHz,CDCl3)5l2.5,13.9,20.0,22.4,26.4,29.0,31.3,41.1,117.8,134.0,150.1, 151.6,163.7ppm;MS(ESI,m/z):266(M-H)-;Anal.calcd for Ci3H2iN3〇3:C,58.41;H,7.92; N,15.72;Found:C,58.63;H,7.91;N,15.74.
[0065] 实施例5.化合物2.6的合成
[0066] 如实施例1所述方法,制备得化合物2.6,表征数据如下:IR(film)vmax: 3321,3260, 3079,2917,2850,1725,1694,1539,1514,1450,1342,1267,1195(^1? 匪R(400MHz, CDCl3)5〇.91(t,J=6.8Hz,3H),1.33-1.42(m,6H),l.59-1.66(m,2H),3.39-3.44(m,2H), 8.50(d,J = 6.8Hz,lH),9.02(br,lH),9.20(s,lH)ppm;13C NMR(100MHz,CDC13)S13.9,22.5, 26.4.29.1.31.3.41.5.123.0. 123.4.139.6.142.0.149.0.149.9ppm;MS(ESI,m/z):256(M-H)-;Anal.calcd for CiiHi6FN3〇3:C,51.36;H,6.27;N,16.33;Found:C,51.19;H,6.28;N, 16.26.
[0067] 实施例6.化合物2.7的合成
[0068] 如实施例1所述方法,制备得化合物2.7,表征数据如下:IR(f ilm) vmax: 3309,3068, 2914,2844,1756,1719,1687,1633,1571,1536,1331,1294,1084,1046cm-S 1!! NMR(400MHz, CDCl3)50.88-0.92(m,3H),1.26-1.38(m,6H),1.58-1.65(m,2H),3.39-3.44(m,2H),5.01 (s,lH),8.83(br,lH),9.02(s,lH)ppm; 13C NMR(100MHz,CDC13)S13.9,22.5,26.4,29.0, 31.3.41.8.93.0. 111.5.147.0.147.8.149.7.157.6ppm;MS(ESI,m/z):263(M-H)-; Anal.calcd for Ci2Hi6N4〇3:C,54.54;H,6.10;N,21.20;Found:C,54.70;H,6.11;N,21.18.
[0069] 实施例7.化合物2.8的合成
[0070] 如实施例1所述方法,制备得化合物2.8,表征数据如下:IR(film)vmax: 3288,3189, 3085,2915,2846,1734,1713,1681,1408,1333,121lcm- 1 NMR(400MHz,CDCl3)S0.92(t,J =6.8Hz,3H),1.28-1.44(m,6H),1.60-1.65(m,2H),2.64(s,3H),3.41-3.46(m,2H),8.39 (s,lH),8.93(br,lH),9.27(s,lH)ppm ;13C NMR(100MHz,CDC13)S14.0,22.5,26.5,29.1, 30.6,31·3,41.6,114.2,145.4,148.7,150.6,159.8,192.9ppm;MS(ESI,m/z):280(M-H)- ; Anal.calcd for C13H19N3O4:C,55.50;H,6.81;N,14.94;Found:C,55.64;H,6.80;N,14.95.
[0071] 实施例8.化合物2.11的合成
[0072] 如实施例1所述方法,制备得化合物2.11,表征数据如下:IR(f i lm) vmax: 3313, 3253,2953,2917,2849,1727,1693,1577,1541,1466,1383,1266,1199cm- 1;咕 NMR(400MHz, CDCl3)50.89(t,J=6.8Hz,3H),1.31-1.38(m,6H),1.56-1.63(m,2H),2.30(s,3H),3.36-3.41(m,2H),8.39(s,lH),9.08(t,J = 5.2Hz,lH),10.03(s,lH)ppm;13C NMR(100MHz,CDC13) δ13·8,20·0,22·4,26·3,29·0,31·2,41·3,128·1,130·2,149·2,150·6,158·2,168·3ppm;MS (ESI,m/z):296(M-H)_; Anal, calcd for C13H19N3O5: C, 52.52 ;H,6.44 ;N, 14.13 ;Found: C, 52.33;H,6.43;N,14.15.
[0073] 实施例9.化合物2.12的合成
[0074] 如实施例1所述方法,制备得化合物2.12,表征数据如下:11?(^111)~^ 3263, 3182,3068,2950,2917,2849,1758,1735,1704,1690,1543,1536,1352,1287,1101〇11 _1;^ NMR(400MHz,CDCl3)S0.89(t,J = 6.8Hz,3H) ,1.29-1.38(m,6H) ,1.57-1 ·62(ι?,2H),2.09(s, 3H),3.37-3.42(m,2H),4.93(s,2H),8.56(s,lH),9.09(t,J=5.2Hz,lH),9.81(s,lH)ppm; 13C 匪R(100MHz,CDCI3)δ 13 ·9,20·8,22·4,26·4,29·0,31·3,41·3,58·5,111·1,138·6, 149.5,151.3,162.2,170.6ppm;MS(ESI,m/z):310(M-H)-;Anal .calcd for Ci4H2iN3〇5:C, 54.01;Η,6·80;N,13.50;Found:C,54.20;Η,6·81;N,13.48·
[0075] 实施例10.化合物2.13的合成
[0076] 如实施例1所述方法,制备得化合物2.13,表征数据如下:11?(^111)~^ 3295, 2917,2849,1743,1735,1572,1546,1263,1094(^5? 匪R(400MHz,CDC13)S0.89(t,J = 6.8Hz,3H),1.26-1.38(m,6H),1.56-1.64(m,2H),2.19(s,3H),3.37-3.42(m,2H),7.56(s, 1H),9.00(br,lH),9.48(s,lH)ppm; 13C NMR(100MHz,CDC13)S14.0,22.5,24.1,26.5,29.1, 31.4,41.4,115.4,125.2,149.4,149.7,159.3,168.2ppm;MS(ESI,m/z):295(M-H) -; Anal.calcd for C13H20N4O4:C,52.69;H,6.80;N,18.91;Found:C,52.49;H,6.79;N,18.89.
[0077] 实施例11.化合物2.14的合成
[0078] 如实施例1所述方法,制备得化合物2.14,表征数据如下:11?(^111)~^:3307, 3254,3112,2955,2919,2850,1730,1663,1546,1476,1384,1277,1258,1097(^5? 匪R (400MHz,CDCl3)S0.86(t,J = 6.8Hz,3H),l .27-1.31(m,6H) ,1.48-1 ·51(ι?,2H) ,3.23-3.28 (m,2H),7.70(s,lH),9.21(s,lH),9.24(t,J = 5.6Hz,lH),11.88(s,lH)ppm;13C NMR (100MHz,CDC13)δ 14.3,22.5,26.4,29.2,31.3,40.7,117.0,133.9,150.6,150.9, 160.5ppm;MS(ESI,m/z):254(M-H) _;Anal.calcd for C11H17N3O4: C,51.76;H,6.71;N, 16.46;Found:C,51.90;H,6.70;N,16.49·
[0079] 实施例12.化合物2.15的合成
[0080] 如实施例1所述方法,制备得化合物2.15,表征数据如下:4匪R(400MHz,⑶α3)δ 0.86(t,J=6.8Hz,3H),1.23-1.31(m,6H),1.46-1.51(m,2H),3.23-3.28(m,2H),4.48(s, 2H),7.57(s,lH),9.30(t,J = 5.6Hz,lH),11.81(s,lH)ppm;13C NMR(100MHz,CDC13)S14.3, 22.5.26.4.29.2.31.3.40.7.112.2.124.5.150.8.151.0. 160.9ppm;MS(ESI,m/z):253(M-H) - ;HRMS(ESI)calcd for[CiiHi7N403] + (M-H)-:253.1301;found:253.1295.
[0081] 实施例13.化合物2.16的合成
[0082] 如实施例1所述方法,制备得化合物2.16,表征数据如下:4匪R(400MHz,⑶α3)δ 0.88(t,J=6.8Hz,3H),1.30-1.40(m,6H),1.56-1.65(m,2H),2.40(br,lH),3.37-3.42(m, 2H),4.50(d,J = 6.8Hz,2H),8.33(s,lH),8.45(s,lH),8.98(s,lH)ppm;13C 匪R(100MHz, αχη3)δ14·1,22.7,26.6,29.3,31.5,41.5,58.9,115.2,136.2,149.7,151.1,162.5ppm;MS (ESI,m/z): 268 (M-H)-; Anal · cal cd for C12H19N3O4 :C,53.52;H,7.11;N,15.60; Found: C, 53.36;H,7.12;N,15.58.
[0083] 实施例14.化合物3.5的合成
[0084] 如实施例1所述方法,制备得化合物3.5,表征数据如下:IR(f ilm)vmax: 3086,2918, 2849,1779,1747,1696,1537,1436,1334,1268,1188,1096cm-1; 4 匪R(400MHz,DMS0-d6)S 1.52-1.63(m,4H),2.23(s,3H),2.60(t,J=7.6Hz,2H),3.28-3.33(m,2H),7.14-7.21(m, 3H),7.24-7.29(m,2H),8.26(br,lH),9.12(t,J = 6.0Hz,lH) ,12.17(s,lH)ppm;13C 匪R (100MHz,DMS0-d
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