Page 25 of 53
Journal of Medicinal Chemistry
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5.4 Hz, 1H), 6.98 (d, J = 3.2 Hz, 1H). C NMR (151 MHz, DMSO) δ 154.68, 152.99, 140.47,
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39.37, 138.15, 134.10, 132.35, 132.01, 130.36, 129.38, 128.68, 127.08, 124.58, 123.89,
22.29, 121.45, 120.89, 116.80, 99.27, 14.71. Anal. Calcd. for C22 S: C, 76.93; H, 5.58;
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H N
N, 8.16. Found: C, 77.31; H, 5.48; N, 7.99.
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Nꢀ(3ꢀ((2ꢀphenylquinolinꢀ4ꢀyl)amino)phenyl)acetamide (30). The title compound was
synthesized from 4ꢀchloroꢀ2ꢀphenylquinoline (240 mg, mmol) and Nꢀ(3ꢀ
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aminophenyl)acetamide (150 mg, 1 mmol) to yield 30 as pale yellow solid (136 mg, 38%),
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mp 281 °C (decomposition). H NMR (500 MHz, DMSOꢀd
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) δ 14.25 (s, 1H), 11.05 (s, 1H),
10.38 (s, 1H), 8.85 (dd, J = 8.6, 1.3 Hz, 1H), 8.35 (dd, J = 8.6, 1.1 Hz, 1H), 8.08 – 8.01 (m,
1H), 7.98 (d, J = 2.1 Hz, 1H), 7.96 – 7.91 (m, 2H), 7.82 – 7.76 (m, 1H), 7.68 – 7.58 (m, 3H),
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.52 – 7.43 (m, 2H), 7.23 (dt, J = 7.2, 1.9 Hz, 1H), 7.05 (s, 1H), 2.08 (s, 3H). C NMR (126
MHz, DMSO) δ 168.89, 154.61, 153.04, 140.80, 139.35, 137.52, 134.10, 132.39, 132.00,
30.23, 129.38, 128.67, 127.09, 123.66, 120.89, 119.61, 117.85, 116.73, 115.58, 99.01, 24.17.
Anal. Calcd. for C23 O: C, 77.94; H, 5.69; N, 11.86. Found: C, 78.20; H, 5.65; N, 11.97.
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H N
4ꢀ((2ꢀphenylquinolinꢀ4ꢀyl)amino)benzonitrile (31). The title compound was synthesized
from 4ꢀchloroꢀ2ꢀphenylquinoline (240 mg, 1 mmol) and 4ꢀaminobenzonitrile (118 mg, 1
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mmol) to yield 31 as pale yellow solid (170 mg, 53%), mp 290 °C (decomposition). H NMR
(500 MHz, DMSOꢀd
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) δ 14.53 (s, 1H), 11.21 (s, 1H), 8.87 (d, J = 8.6 Hz, 1H), 8.38 (d, J = 8.5
Hz, 1H), 8.06 (t, J = 7.7 Hz, 1H), 8.02 – 7.93 (m, 4H), 7.82 (t, J = 9.0 Hz, 3H), 7.74 – 7.58 (m,
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H), 7.33 (s, 1H). C NMR (126 MHz, DMSO) δ 156.48, 148.43, 142.42, 137.61, 131.24,
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30.26, 129.83, 129.02, 128.05, 127.50, 124.69, 123.66, 118.99. C NMR (126 MHz, DMSO)
δ 153.65, 142.62, 134.14, 132.05, 129.33, 128.85, 127.34, 124.58, 123.89, 118.78, 117.58,
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00.74. Anal. Calcd. for C22
2.82.
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H N : C, 81.96; H, 5.00; N, 13.03. Found: C, 81.73; H, 5.39; N,
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