Molecules 2019, 24, 2812
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(2E)-N-(3-chlorophenyl)-N'-{4-[(7-chloroquinolin-4-yl)amino]butyl}but-2-enediamide (13). Reaction
conditions: 16 h, room temperature. From the reaction of 0.094 g acid 10 and 0.038 g (0.297 mmol)
3-chloroaniline and after purification by column chromatography (mobile phase
dichloromethane/methanol 8.5:1.5) and crystallization from ether, followed by crystallization from
methanol, 0.032 g (26%) of white solid 13 was obtained; mp 232 °C (decomp.); IR (KBr): νmax 3340,
3298, 3182, 3092, 3032, 2944, 2866, 2830, 2360, 1650, 1592 1542, 1482, 1426, 1334, 1234, 1214, 1170, 1142,
–1
1
1078, 1034, 970, 900, 848, 808, 782, 678, 626, 588, 558 cm ; H-NMR (DMSO-d6) δ 10.67 (s, 1H), 8.56 (t,
1H, J = 5.5 Hz), 8.43 (d, 1H, J = 5.9 Hz), 8.38 (d, 1H, J = 9.1 Hz), 8.01–7.87 (m, 2H), 7.83 (d, 1H, J = 2.1
Hz), 7.66–7.46 (m, 2H), 7.37 (t, 1H, J = 8.1 Hz), 7.15 (dd, 1H, J = 7.9, 1.1 Hz), 7.02 (q, 2H, J = 14.5 Hz),
13
6.60 (d, 1H, J = 6.0 Hz), 3.42–3.32 (m, 2H), 3.29–3.19 (m, 2H), 1.76–1.53 (m, 4H); C-NMR (DMSO-d6) δ
163.34, 162.64, 151.57, 149.35, 146.10, 140.25, 134.66, 134.42, 133.14, 132.33, 130.56, 125.10, 124.79,
124.56, 123.53, 118.79, 117.78, 116.88, 98.66, 42.26, 38.50, 26.52, 25.18; ESI-MS: m/z calculated for
+
C23H22Cl2N4O2: 456.11, found: 457.0 (M + 1) ; Anal. Calcd. C23H22Cl2N4O2: C, 60.40; H, 4.85; N, 12.25.
Found: C, 60.26; H, 4.62; N, 12.27.
(2E)-N-(4-chlorophenyl)-N'-{4-[(7-chloroquinolin-4-yl)amino]butyl}but-2-enediamide (14). Reaction
conditions: 1 h, 65 °C, MW. From the reaction of 0.094 g acid 10 and 0.038 g (0.297 mmol)
4-chloroaniline and after crystallization from methanol, 0.088 g (71%) of white solid 14 was obtained;
mp 237 °C (decomp.); IR (KBr): νmax 3412, 3286, 3186, 3098, 3072, 2946, 2878, 2706, 2364, 1363, 1544,
–1
1
1492, 1452, 1398, 1342, 1240, 1212, 1172, 1128, 1094, 1014, 986, 842, 76, 680, 584, 558, 506 cm ; H-NMR
(DMSO-d6) δ 10.71 (s, 1H), 9.51 (t, 1H, J = 5.2 Hz), 8.66 (d, 1H, J = 9.2 Hz), 8.60 (t, 1H, J = 5.6 Hz), 8.55
(d, 1H, J = 7.1 Hz), 8.04 (d, 1H, J = 2.0 Hz), 7.75 (dd, 3H, J = 12.8, 5.5 Hz), 7.39 (d, 2H, J = 8.9 Hz), 7.02
(q, 2H, J = 15.1 Hz), 6.89 (d, 1H, J = 7.2 Hz), 3.6–3.5 (m, 2H), 3.27–3.14 (m, 2H), 1.79–1.66 (m, 2H),
13
1.65–1.53 (m, 2H); C-NMR (DMSO-d6) δ 163.43, 162.42, 155.17, 143.06, 138.87, 137.81, 134.13, 132.50,
128.73, 127.35, 126.68, 125.74, 120.87, 119.30, 115.50, 98.59, 42.79, 38.34, 26.32, 25.01; ESI-MS: m/z
+
calculated for C23H22Cl2N4O2: 456.11, found: 457.0 (M + 1) ; Anal. Calcd. C23H22Cl2N4O2: C, 60.40; H,
4.85; N, 12.25. Found: C, 60.34; H, 4.97; N, 12.13.
(2E)-N'-{4-[(7-chloroquinolin-4-yl)amino]butyl}-N-[3-(trifluoromethyl)phenyl]but-2-enediamide (15).
Reaction conditions: 24 h, room temperature. From the reaction of 0.094 g acid 10 and 0.048 g (0.297
mmol) 3-trifluoroaniline and after purification by column chromatography (mobile phase
dichloromethane/methanol 8.5:1.5) after crystallization from ether, 0.034 g (26%) of white solid 15
was obtained; mp 240 °C (decomp.); IR (KBr): νmax 3418, 3210, 3072, 3002, 2958, 1620, 1550, 1490, 1414,
–1
1
1312, 1182, 1136, 1068, 1022, 840, 656, 558 cm ; H-NMR (DMSO-d6) δ 10.81 (s, 1H), 9.26 (t, 1H, J = 5.2
Hz), 8.62–8.53 (m, 4H), 7.94 (d, 1H, J = 2.1 Hz), 7.86 (d, 1H, J = 8.4 Hz, 1H), 7.81 (dd, 1H, J = 9.1, 2.1
Hz), 7.62 (t, 1H, J = 8.0 Hz), 7.49 (d, 1H, J = 7.8 Hz), 7.04 (q, 2H, J = 14.88 Hz), 6.93 (d, 1H, J = 7.1 Hz),
13
3.61–3.54 (m, 2H), 3.32–3.25 (m, 2H), 1.81–1.70 (m, 2H), 1.68–1.58 (m, 2H); C-NMR (DMSO-d6) δ
163.31, 162.78, 155.08, 143.56, 139.54, 139.14, 137.77, 134.47, 132.27, 130.17, 129.64-129.38 (q, J = 26.85
Hz), 126.75, 125.45, 122.93, 122.71-120.00 (q, J = 274.54 Hz), 120.22, 119.67, 115.53, 115.36, 98.68, 42.85,
+
38.41, 26.34, 25.06; ESI-MS: m/z calculated for C24H22ClF3N4O2: 490.14, found: 491.1 (M + 1) ; Anal.
Calcd. C24H22ClF3N4O2: C, 58.72; H, 4.52; N, 11.41. Found: C, 58.90; H, 4.55; N, 11.58.
(2E)-N'-{4-[(7-chloroquinolin-4-yl)amino]butyl}-N-[4-(trifluoromethyl)phenyl]but-2-enediamide (16).
Reaction conditions: 24 h, room temperature. From the reaction of 0.094 g acid 10 and 0.048 g (0.297
mmol) 4-trifluoroaniline and after crystallization from water, followed by crystallization from ether,
0.049 g (37%) of white solid 16 was obtained; mp 270 °C (decomp.); IR (KBr): νmax 3254, 2972, 2914,
2836, 2760, 2722, 2546, 2488, 2426, 2362, 2098, 1976, 1712, 1610, 1590, 1544, 1472, 1442, 1398, 1324,
–1
1
1210, 1154, 1104, 1066, 1018, 978, 956, 882, 842, 802, 768, 686, 650, 592, 508 cm ; H-NMR (DMSO-d6) δ
10.92 (s, 1H), 9.30 (t, 1H, J = 2.54 Hz), 8.71–8.57 (m, 2H), 8.54 (d, 1H, J = 6.9 Hz), 8.01 (d, 1H, J = 2.0 Hz),
7.91 (d, 2H, J = 8.5 Hz), 7.73 (dd, 3H, J = 14.2, 5.2 Hz), 7.06 (q, 2H, J = 15.1 Hz), 6.86 (d, 1H, J = 7.0 Hz),
13
3.57–3.49 (m, 2H), 3.29–3.21 (m, 2H), 1.77–1.67 (m, 2H), 1.64–1.54 (m, 2H); C-NMR (DMSO-d6) δ
163.35, 162.88, 155.08, 143.26, 142.39, 139.08, 137.70, 134.62, 132.29, 126.65, 126.17, 125.70,
123.95–123.52 (q, J = 25.48 Hz), 122.53–118.93 (q, J = 270.75 Hz), 119.48–119.33 (q, J = 10.26), 115.54,
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