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GEZEGEN ET AL.
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1‐{4‐[5‐Cyano‐6‐ethoxy‐4‐(4‐methoxyphenyl)pyridin‐2‐yl]phenyl}‐3‐
phenylurea (10c)
138.93, 136.56, 130.51, 130.42, 129.29 (2C), 129.12 (2C), 129.03
(2C), 128.82 (2C), 126.38, 121.47 (2C), 118.52 (2C), 116.34, 114.65,
91.90, 67.04, 14.86. Anal. calc. for C27H21ClN4O2: C, 69.15; H, 4.51;
N, 11.95. Found: C, 69.03; H, 4.38; N, 11.82.
Yield: 91%, Mp: 194–197°C. IR (KBr, cm−1): 3400, 2218, 1725, 1584,
1538, 1442, 1375, 1339, 1314, 1233, 1174, 1024, 823, 748, 682,
634, 574. 1H NMR (400 MHz, DMSO‐d6): δ = 8.98 (s, 1H), 8.74 (s,
1H), 8.19 (d, J = 8.4 Hz, 2H), 7.72 (d, J = 8.4 Hz, 2H), 7.68 (s, 1H), 7.62
(d, J = 8.4 Hz, 2H), 7.47 (d, J = 7.2 Hz, 2H), 7.30 (t, J = 8.0 Hz, 2H), 7.14
(d, J = 8.4 Hz, 2H), 7.00 (t, J = 7.2 Hz, 1H), 4.63 (dd, J = 14.0, 7.2 Hz,
2H), 3.86 (s, 3H), 1.45 (t, J = 7.6 Hz, 3H). 13C NMR (100 MHz,
DMSO‐d6): δ = 164.56, 161.21, 157.38, 156.19, 152.77, 142.69,
139.90, 130.60 (2C), 130.46, 129.26 (2C), 128.74 (2C), 128.66,
122.56, 118.87 (2C), 118.38 (2C), 116.30, 114.74 (2C), 112.79,
91.26, 63.33, 55.89, 14.87. Anal. calc. for C28H24N4O3: C, 72.40; H,
5.21; N, 12.06. Found: C, 72.37; H, 5.18; N, 12.01.
1‐(4‐Chlorophenyl)‐3‐{4‐[5‐cyano‐6‐ethoxy‐4‐(p‐tolyl)pyridin‐2‐
yl]phenyl}urea (11b)
Yield: 94%, Mp: 244–247°C. IR (KBr, cm−1): 3338, 2227, 1694, 1694,
1581, 1535, 1492, 1444, 1397, 1377, 1338, 1310, 1237, 1214, 1177,
1145, 1089, 1034, 1011, 819, 616, 508. 1H NMR (400 MHz,
DMSO‐d6): δ = 9.03 (s, 1H), 8.90 (s, 1H), 8.20 (d, J = 8.0 Hz, 2H), 7.70
(s, 1H), 7.65–7.61 (m, 4H), 7.51 (d, J = 8.0 Hz, 2H), 7.40 (d, J = 8.0 Hz,
2H), 7.34 (d, J = 8.4 Hz, 2H), 4.63 (dd, J = 14.0, 7.2 Hz, 2H), 2.48 (s,
3H), 1.44 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, DMSO‐d6):
δ = 164.50, 157.48, 156.62, 152.69, 142.55, 140.31, 138.93, 133.68,
130.58, 129.85 (2C), 129.13 (2C), 128.95 (2C), 128.79, 127.32,
126.12, 120.41 (2C), 118.53 (2C), 116.11, 112.97, 91.58, 63.40,
21.36, 14.86. Anal. calc. for C28H23ClN4O2: C, 69.63; H, 4.80; N,
11.60. Found: C, 69.59; H, 4.78; N, 11.53.
1‐{4‐[4‐(4‐Chlorophenyl)‐5‐cyano‐6‐ethoxypyridin‐2‐yl]phenyl}‐3‐
phenylurea (10d)
Yield: 89%, Mp: 215–218°C. IR (KBr, cm−1): 3316, 2979, 2357, 2222,
1649, 1597, 1544, 1495, 1443, 1424, 1379, 1342, 1314, 1234, 1206,
1093, 1035, 1013, 821, 745, 693, 647, 509, 484. 1H NMR (400 MHz,
DMSO‐d6): δ = 8.89 (s, 1H), 8.73 (s, 1H), 8.14 (d, J = 8.8 Hz, 2H), 7.93
(d, J = 8.4 Hz, 2H), 7.78 (s, 1H), 7.60–7.57 (m, 4H), 7.47 (d, J = 7.6 Hz,
2H), 7.30 (t, J = 8.4 Hz, 2H), 6.99 (t, J = 7.6 Hz, 1H), 4.49 (dd, J = 14.0,
7.2 Hz, 2H), 1.40 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, DMSO‐d6):
δ = 164.20, 154.89, 152.88, 150.39, 141.28, 140.04, 136.89, 134.51,
132.08, 130.98, 129.45 (2C), 129.37 (2C), 129.27 (2C), 127.79 (2C),
122.44, 118.78 (2C), 118.40 (2C), 110.52, 106.03, 61.69, 15.07. Anal.
calc. for C27H21ClN4O2: C, 69.15; H, 4.51; N, 11.95. Found: C, 69.10;
H, 4.48; N, 11.86.
1‐(4‐Chlorophenyl)‐3‐{4‐[5‐cyano‐6‐ethoxy‐4‐(4‐methoxyphenyl)-
pyridin‐2‐yl]phenyl}urea (11c)
Yield: 90%, Mp: 265–268°C. IR (KBr, cm−1): 3381, 1722, 1607, 1578,
1535, 1494, 1445, 1315, 1295, 1259, 1236, 1174, 1024, 870, 827,
637, 517, 501. 1H NMR (400 MHz, DMSO‐d6): δ = 8.77 (s, 1H), 8.64
(s, 1H), 8.04 (d, J = 8.4 Hz, 2H), 7.60 (d, J = 8.4 Hz, 2H), 7.53 (d,
J = 8.4 Hz, 2H), 7.47 (s, 1H), 7.41 (d, J = 8.4 Hz, 2H), 7.18 (d, J = 8.4 Hz,
2H), 7.02 (d, J = 8.4 Hz, 2H), 4.57 (dd, J = 14.0, 7.2 Hz, 2H), 3.81 (s,
3H), 1.43 (t, J = 7.2 Hz, 3H). 13C NMR (100 MHz, DMSO‐d6):
δ = 164.51, 161.00, 157.26, 155.93, 152.52, 142.22, 138.59, 130.62,
130.14 (2C), 128.75 (2C), 128.65 (2C), 128.31, 126.35, 120.02 (2C),
118.28 (2C), 116.01, 114.42 (2C), 112.39, 91.36, 63.06, 55.55, 14.72.
Anal. calc. for C28H23ClN4O3: C, 67.40; H, 4.65; N, 11.23. Found: C,
67.34; H, 4.59; N, 11.18.
1‐{4‐[4‐(4‐Bromophenyl)‐5‐cyano‐6‐ethoxypyridin‐2‐yl]phenyl}‐3‐
phenylurea (10e)
Yield: 93%, Mp: 217–220°C. IR (KBr, cm−1): 3416, 2923, 1645, 1597,
1542, 1496, 1444, 1377, 1341, 1314, 1236, 1209, 820, 745, 693. 1H
NMR (400 MHz, DMSO‐d6): δ = 8.90 (s, 1H), 8.74 (s, 1H), 8.14 (d,
J = 8.4 Hz, 2H), 7.86 (d, J = 8.4 Hz, 2H), 7.77 (s, 1H), 7.71 (d, J = 8.4 Hz,
2H), 7.59 (d, J = 8.4 Hz, 2H), 7.49 (d, J = 8.0 Hz, 2H), 7.30 (t, J = 8.0 Hz,
2H), 6.97 (t, J = 6.8 Hz, 1H), 4.47 (dd, J = 14.0, 6.8 Hz, 2H), 1.40 (t,
J = 6.8 Hz, 3H). 13C NMR (100 MHz, DMSO‐d6): δ = 164.22, 154.93,
152.89, 150.46, 141.35, 140.10, 136.99, 132.37 (2C), 132.24, 131.18,
129.64 (2C), 129.26 (2C), 127.78 (2C), 123.19, 122.43, 118.79 (2C),
118.42 (2C), 110.46, 105.98, 61.69, 15.07. Anal. calc. for C27H21BrN4O2:
C, 63.17; H, 4.12; N, 10.91. Found: C, 63.08; H, 4.09; N, 10.81.
1‐(4‐Chlorophenyl)‐3‐{4‐[4‐(4‐chlorophenyl)‐5‐cyano‐6‐
ethoxypyridin‐2‐yl]phenyl}urea (11d)
Yield: 86%, Mp: 266–263°C. IR (KBr, cm−1): 3304, 2975, 1644, 1595,
1546, 1491, 1427, 1398, 1379, 1344, 1303, 1236, 1207, 1090, 1012,
821, 654, 515, 482. 1H NMR (400 MHz, DMSO‐d6): δ = 8.62 (s, 1H),
8.57 (s, 1H), 7.98 (d, J = 8.4 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H), 7.50 (s,
1H), 7.49 (d, J = 8.4 Hz, 2H), 7.41 (m, 2H), 7.16 (d, J = 8.4 Hz, 2H), 7.02
(d, J = 8.4 Hz, 2H), 4.57 (dd, J = 14.0, 7.2 Hz, 2H), 1.43 (t, J = 7.2 Hz,
3H). 13C NMR (100 MHz, DMSO‐d6): δ = 164.08, 154.77, 152.65,
150.35, 140.77, 138.66, 137.07, 134.60, 132.44, 129.17 (2C), 128.71
(2C), 128.68 (2C), 127.42 (2C), 126.28, 119.92 (2C), 118.31 (2C),
110.25, 106.07, 92.44, 61.50, 14.89. Anal. calc. for C27H20Cl2N4O2:
C, 64.42; H, 4.00; N, 11.13. Found: C, 64.38; H, 3.89; N, 11.10.
1‐(4‐Chlorophenyl)‐3‐[4‐(5‐cyano‐6‐ethoxy‐4‐phenylpyridin‐2‐
yl)phenyl]urea (11a)
Yield: 89%, Mp: 268–271°C. IR (KBr, cm−1): 3410, 2222, 1585, 1540,
1491, 1445, 1399, 1373, 1339, 1309, 1234, 1175, 828, 762, 698,
607, 505. 1H NMR (400 MHz, DMSO‐d6): δ = 9.05 (s, 1H), 8.92 (s,
1H), 8.22 (d, J = 8.8 Hz, 2H), 7.75–7.73 (m, 3H), 7.62 (d, J = 8.8 Hz,
2H), 7.60–7.58 (m, 3H), 7.51 (d, J = 8.8 Hz, 2H), 7.34 (d, J = 8.8 Hz,
2H), 4.65 (dd, J = 14.0, 6.8 Hz, 2H), 1.46 (t, J = 6.8 Hz, 3H). 13C NMR
(100 MHz, DMSO‐d6): δ = 164.44, 157.57, 156.66, 152.69, 142.60,
1‐(4‐Chlorophenyl)‐3‐{4‐[4‐(4‐bromophenyl)‐5‐cyano‐6‐
ethoxypyridin‐2‐yl]phenyl}urea (11e)
Yield: 81%, Mp: 272–274°C. IR (KBr, cm−1): 3300, 2968, 1621, 1585,
1541, 1487, 1426, 1389, 1374, 1338, 1300, 1236, 1201, 1089, 1009,