2H), 2.39 (m, 4H), 2.16 (s, 3H), 2.04 – 1.93 (m, 2H). MS (ESI) m/z (%): 678.0 [M+H]+; Anal. calcd. for
C35H34F3N5O6 (%):C, 62.03; H, 5.06; N, 10.33; Found (%): C, 62.35; H, 5.08; N, 10.11.
7.6.17. 1-(3,4-difluorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperidin-1-yl)propoxy)quinolin-4-
yl)oxy)phenyl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxamide (44)
Yield: 64.9%; M.p.:109–111 °C; 1H NMR (600 MHz, CDCl3) δ 8.47 (d, J = 5.1 Hz, 1H), 7.94 (s, 1H), 7.75 (dd,
J = 10.5, 2.1 Hz, 1H), 7.56 (s, 1H), 7.42 (s, 1H), 7.30 (t, J = 9.0 Hz, 2H), 7.25 (m, 1H), 7.17 – 7.08 (m, 1H), 7.03 (d,
J = 8.1 Hz, 1H), 6.40 (d, J = 5.0 Hz, 1H), 4.24 (t, J = 6.5 Hz, 2H), 4.04 (s, 3H), 3.49 (s, 3H), 2.91 (d, J = 10.7 Hz,
2H), 2.54 (t, J = 7.2 Hz, 2H), 2.25 (s, 3H), 2.18 – 2.08 (m, 2H), 1.94 (t, J = 11.3 Hz, 2H), 1.62 (d, J = 12.1 Hz, 2H),
1.40 – 1.31 (m, 1H), 1.24 (d, J = 10.2 Hz, 2H), 0.92 (d, J = 6.3 Hz, 3H). MS (ESI) m/z (%): 690.0 [M+H]+; Anal.
calcd. for C37H38F3N5O5 (%): C, 64.43; H, 5.55; N, 10.15; Found (%): C, 64.49; H, 5.45; N, 10.21.
7.6.18. 1-(3,4-difluorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinolin-4-
yl)oxy)phenyl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxamide (45)
Yield: 68.8%; M.p.:118–120 °C; IR (KBr) cm-1: 3418.6, 2935.0, 2801.7, 2320.3, 1698.2, 1670.3, 1580.6,
1508.6, 1480.0, 1431.7, 1349.3, 1304.8, 1249.8, 1211.2, 1164.6, 1120.6, 1096.1,949.9, 853.6,779.7; 1H NMR (600
MHz, CDCl3) δ 8.45 (d, J = 5.0 Hz, 1H), 7.92 (s, 1H), 7.73 (dd, J = 11.8, 2.2 Hz, 1H), 7.54 (s, 1H), 7.43 (s, 1H),
7.29 (t, J = 9.0 Hz, 2H), 7.24 (m, 1H), 7.15 – 7.07 (m, 1H), 7.03 (d, J = 8.1 Hz, 1H), 6.41 (d, J = 5.1 Hz, 1H), 4.23
(t, J = 6.5 Hz, 2H), 4.02 (s, 3H), 3.49 (s, 3H), 2.78 – 2.35 (m, 10H), 2.38 (s, 3H), 2.26 (s, 3H), 2.19 – 2.08 (m, 2H).
MS (ESI) m/z (%): 690.8 [M+H]+; Anal. calcd. for C36H37F3N6O5 (%): C, 62.60; H, 5.40; N, 12.17; Found (%): C,
62.49; H, 5.45; N, 12.21.
7.6.19. 1-(3-chloro-4-fluorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperidin-1-yl)propoxy)quino
lin-4-yl)oxy)phenyl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxamide (46)
1
Yield: 65.9%; M.p.:117–119 °C; H NMR (400 MHz, CDCl3) δ 8.50 (d, J = 5.3 Hz, 1H), 7.78 (dd, J = 10.5,
2.0 Hz, 1H), 7.71 (s, 1H), 7.58 (s, 1H), 7.45 (s, 1H), 7.40 (dd, J = 6.5, 2.3 Hz, 1H), 7.34 – 7.28 (m, 2H), 7.26 – 7.24
(m, 1H), 7.23 – 7.17 (m, 1H), 6.42 (d, J = 5.2 Hz, 1H), 4.27 (t, J = 6.7 Hz, 2H), 4.07 (s, 3H), 3.53 (s, 3H), 2.94 (d, J
= 11.2 Hz, 2H), 2.56 (t, J = 7.3 Hz, 2H), 2.29 (s, 3H), 2.22 – 2.10 (m, 2H), 1.97 (t, J = 10.8 Hz, 2H), 1.65 (d, J =
12.6 Hz, 2H), 1.43 – 1.31 (m, 1H), 1.30 – 1.19 (m, 2H), 0.94 (d, J = 6.3 Hz, 3H). MS (ESI) m/z (%): 705.8 [M+H]+;
Anal. calcd. for C37H38ClF2N5O5 (%): C, 62.93; H, 5.42; N, 9.92; Found (%): C, 62.98; H, 5.35; N, 10.01.
7.6.20. 1-(3-chloro-4-fluorophenyl)-N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinli
n-4-yl)oxy)phenyl)-3,5-dimethyl-2-oxo-2,3-dihydro-1H-imidazole-4-carboxamide (47)
Yield: 66.4%; M.p.:131–133 °C; IR (KBr) cm-1: 3422.0, 2936.3, 2879.6, 2797.7, 1698.2, 1669.8, 1620.2,
1504.5, 1479.4, 1431.1, 1348.6, 1283.2, 1250.0, 1210.7, 1164.4, 1122.1, 1097.8, 871.8; 1H NMR (400 MHz, CDCl3)
δ 8.49 (d, J = 5.3 Hz, 1H), 7.83 (s, 1H), 7.75 (dd, J = 11.8, 2.2 Hz, 1H), 7.57 (s, 1H), 7.43 (s, 1H), 7.36 (dd, J = 6.3,
2.5 Hz, 1H), 7.32 – 7.28 (m, 2H), 7.24 (d, J = 8.8 Hz, 1H), 7.20 – 7.14 (m, 1H), 6.41 (d, J = 4.8 Hz, 1H), 4.26 (t, J
= 6.7 Hz, 2H), 4.05 (s, 3H), 3.51 (s, 3H), 2.70 – 2.31 (m, 10H), 2.30 (s, 3H), 2.27 (s, 3H), 2.19 – 2.08 (m, 2H). 13
C
NMR (101 MHz, DMSO) δ 159.78, 158.99, 158.53, 156.07, 155.12, 152.68, 152.41, 152.23, 150.03, 149.31,
146.85, 131.72, 129.34, 124.59, 123.92, 120.61, 120.43, 118.11, 117.90, 117.11, 116.77, 114.88, 109.16, 108.96,
99.46, 67.19, 56.25, 55.26 (2C), 54.83, 53.22 (2C), 46.23, 29.45, 26.53, 11.51. MS (ESI) m/z (%): 707.0 [M+H]+;
Anal. calcd. for C36H37ClF2N6O5 (%): C, 61.14; H, 5.27; N, 11.88; Found (%): C, 61.18; H, 5.32; N, 12.01.
7.6.21. N-(3-fluoro-4-((6-methoxy-7-(3-(4-methylpiperidin-1-yl)propoxy)quinolin-4-yl)oxy)phenyl)-3,5-dim
ethyl-2-oxo-1-(4-(trifluoromethoxy)phenyl)-2,3-dihydro-1H-imidazole-4-carboxamide (48)
1
Yield: 72.8%; M.p.:134–135 °C; H NMR (400 MHz, CDCl3) δ 8.48 (d, J = 5.1 Hz, 1H), 7.77 (dd, J = 11.4,
2.1 Hz, 1H), 7.62 (s, 1H), 7.57 (s, 1H), 7.43 (s, 1H), 7.40 – 7.31 (m, 4H), 7.29 (dd, J = 8.7, 2.1 Hz, 1H), 7.26(m,
1H), 6.41 (d, J = 5.2 Hz, 1H), δ 4.25 (t, J = 6.8 Hz, 2H), 4.05 (s, 3H), 3.53 (s, 3H), 3.03 (d, J = 9.8 Hz, 2H), 2.75 –
2.61 (m, 2H), 2.29 (s, 3H), 2.26 – 2.15 (m, 2H), 2.12 – 1.98 (m, 2H), 1.65 (d, J = 11.2 Hz 2H), 1.48 – 1.29 (m, 3H),
13