Medicinal Chemistry Research
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8.27 (d, J = 5.6 Hz, 1H), 7.46–7.44 (m, 1H), 7.44–7.40 (m,
1H), 7.34 (d, J = 2.2 Hz, 1H), 7.32 (d, J = 2.2 Hz, 1H), 7.11
(d, J = 8.9 Hz, 1H), 7.08 (d, J = 2.2 Hz, 1H), 7.00 (d, J =
5.7 Hz, 1H), 6.96 (d, J = 2.3 Hz, 1H), 6.94 (d, J = 2.1 Hz,
1H), 5.10 (s, 2H), 4.11 (t, J = 6.2 Hz, 2H), 3.49 (t, J =
6.2 Hz, 2H), 3.25 (s, 3H), 2.18 (s, 3H), 2.02–1.95 (m, 2H).
ESI-MS (m/z): 440.2 ([M + H]+).
1103.3, 825.3, 616.4. H NMR (400 MHz, DMSO-d6) δ
8.74 (s, 1H), 8.51 (s, 1H), 8.22 (d, J = 5.5 Hz, 1H), 7.48 (d,
J = 2.2 Hz, 1H), 7.46 (d, J = 2.2 Hz, 1H), 7.35 (d, J =
2.2 Hz, 1H), 7.33 (d, J = 2.1 Hz, 1H), 7.32 (d, J = 2.0 Hz,
1H), 7.30 (d, J = 1.9 Hz, 1H), 7.15 (d, J = 5.5 Hz, 1H), 6.97
(d, J = 2.3 Hz, 1H), 6.95 (d, J = 2.2 Hz, 1H), 5.03 (s, 2H),
3.90 (s, 3H), 3.78 (s, 3H). ESI-MS (m/z): 414.2, 415.2,
416.2, 417.2 ([M + H]+).
1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-{[4-(3-methoxy-
propoxy)-3-methylpyridin-2-yl]methoxy}phenyl}urea (7f)
Yield 37.2% (white solid). m.p.: 179–181 °C. IR(KBr, cm−1):
υ 3421.6, 2922.7, 1694.9, 1590.8, 1544.7, 1511.5, 1484.5,
1462.9, 1418.4, 1384.0, 1326.7, 1311.7, 1293.2, 1217.1,
1-{4-[(3,4-dimethoxypyridin-2-yl)methoxy]phenyl}-3-(4-
methoxyphenyl)urea (7j) Yield 38.9% (white solid). m.p.:
175–176 °C. IR(KBr, cm−1): υ 3422.8, 2922.5, 2852.4,
1599.7, 1561.1, 1509.8, 1384.2, 1299.4, 1226.4, 1110.9,
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1173.4, 1129.3, 1032.4, 826.5, 662.2. H NMR (400 MHz,
1037.6, 829.2, 522.9. H NMR (400 MHz, DMSO-d6) δ
DMSO-d6) δ 9.09 (s, 1H), 8.65 (s, 1H), 8.27 (d, J = 5.6 Hz,
1H), 8.10 (d, J = 2.3 Hz, 1H), 7.64–7.61 (m, 1H), 7.59 (d,
J = 8.8 Hz, 1H), 7.36 (d, J = 2.0 Hz, 1H), 7.34 (d, J = 2.3 Hz,
1H), 7.00 (d, J = 5.7 Hz, 1H), 6.98 (d, J = 2.2 Hz, 1H), 6.96
(d, J = 2.2 Hz, 1H), 5.11 (s, 2H), 4.11 (t, J = 6.2 Hz, 2H),
3.49 (t, J = 6.2 Hz, 2H), 3.25 (s, 3H), 2.18 (s, 3H), 2.02–1.96
(m, 2H). ESI-MS (m/z): 524.3 ([M + H]+).
8.38 (s, 1H), 8.37 (s, 1H), 8.22 (d, J = 5.5 Hz, 1H), 7.35 (s,
1H), 7.34 (s, 1H), 7.32 (s, 1H), 7.31 (s, 1H), 7.15 (d, J =
5.6 Hz, 1H), 6.95 (d, J = 2.2 Hz, 1H), 6.94 (d, J = 2.2 Hz,
1H), 6.86 (d, J = 2.3 Hz, 1H), 6.84 (d, J = 2.2 Hz, 1H), 5.03
(s, 2H), 3.90 (s, 3H), 3.78 (s, 3H), 3.71 (s, 3H). ESI-MS (m/
z): 410.3 ([M + H]+); 432.2 ([M + Na]+).
1-{4-[(3,4-dimethoxypyridin-2-yl)methoxy]phenyl}-3-(4-
fluorophenyl)urea (7k) Yield 48.3% (yellow solid). m.p.:
161–162 °C. IR(KBr, cm−1): υ 3424.9, 2922.8, 2852.8,
1664.8, 1595.7, 1550.6, 1507.0, 1452.7, 1403.4, 1383.8,
1299.9, 1205.9, 1113.4, 1083.5, 1015.5, 832.6, 800.7,
518.3. 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 8.44
(s, 1H), 8.22 (d, J = 5.5 Hz, 1H), 7.46–7.44 (m, 1H), 7.44–
7.41 (m, 1H), 7.34 (d, J = 2.2 Hz, 1H), 7.32 (d, J = 2.2 Hz,
1H), 7.14 (d, J = 5.5 Hz, 1H), 7.11 (d, J = 8.9 Hz, 1H), 7.08
(d, J = 2.1 Hz, 1H), 6.96 (d, J = 2.2 Hz, 1H), 6.95 (d, J =
2.1 Hz, 1H), 5.03 (s, 2H), 3.90 (s, 3H), 3.78 (s, 3H). ESI-
MS (m/z): 398.2, 399.2 ([M + H]+).
1-(3,5-difluorophenyl)-3-{4-[(3,4-dimethoxypyridin-2-yl)
methoxy]phenyl}urea (7g) Yield 46.1% (white solid). m.
p.: 162–164 °C. IR(KBr, cm−1): υ 3422.3, 2921.9, 2852.1,
1609.0, 1559.6, 1511.8, 1490.0, 1434.0, 1384.0, 1301.7,
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1226.0, 1197.0, 1114.4, 1081.7, 1015.7, 832.6, 672.2. H
NMR (400 MHz, DMSO-d6) δ 9.03 (s, 1H), 8.65 (s, 1H),
8.22 (d, J = 5.5 Hz, 1H), 7.35 (d, J = 2.2 Hz, 1H), 7.33 (d,
J = 2.2 Hz, 1H), 7.18 (d, J = 2.3 Hz, 1H), 7.16 (d, J =
2.4 Hz, 1H), 7.14 (d, J = 5.5 Hz, 1H), 6.98 (d, J = 2.3 Hz,
1H), 6.96 (d, J = 2.1 Hz, 1H), 6.79–6.73 (m, 1H), 5.04 (s,
2H), 3.90 (s, 3H), 3.78 (s, 3H). ESI-MS (m/z): 416.3 ([M +
H]+); 438.3 ([M + Na]+).
1-[4-chloro-3-(trifluoromethyl)phenyl]-3-{4-[(3,4-dimethoxy-
pyridin-2-yl)methoxy]phenyl}urea (7l) Yield 40.1% (yel-
lowish solid). m.p.: 106–107 °C. IR(KBr, cm−1): υ 3447.1,
3329.3, 2922.5, 2851.4, 1694.1, 1610.3, 1559.8, 1511.6,
1486.1, 1318.1, 1256.4, 1228.6, 1170.3, 1141.1, 1111.3,
1-{4-[(3,4-dimethoxypyridin-2-yl)methoxy]phenyl}-3-[3-(tri-
fluoromethyl)phenyl]urea (7h) Yield 55.5% (white solid).
m.p.: 149–150 °C. IR(KBr, cm−1): υ 3422.1, 2922.2,
2852.1, 1709.7, 1593.6, 1549.4, 1511.4, 1492.4, 1447.2,
1383.7, 1340.2, 1301.0, 1230.8, 1201.7, 1172.2, 1110.6,
1040.4, 818.4, 795.5, 699.6, 666.6, 617.6. 1H NMR
(400 MHz, DMSO-d6) δ 8.98 (s, 1H), 8.60 (s, 1H), 8.22 (d,
J = 5.5 Hz, 1H), 8.01 (d, J = 2.1 Hz, 1H), 7.59–7.53 (m,
1H), 7.52–7.48 (m, 1H), 7.36 (d, J = 2.3 Hz, 1H), 7.35 (d,
J = 2.1 Hz, 1H), 7.29 (d, J = 7.4 Hz, 1H), 7.15 (d, J =
5.5 Hz, 1H), 6.98 (d, J = 2.2 Hz, 1H), 6.96 (d, J = 2.1 Hz,
1H), 5.04 (s, 2H), 3.90 (s, 3H), 3.78 (s, 3H). ESI-MS (m/z):
448.3 ([M + H]+); 470.2 ([M + Na]+).
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1040.5, 999.7, 874.3, 819.3, 745.2, 686.2, 658.9. H NMR
(400 MHz, DMSO-d6) δ 9.08 (s, 1H), 8.63 (s, 1H), 8.22 (d,
J = 5.5 Hz, 1H), 8.09 (d, J = 2.4 Hz, 1H), 7.64–7.61 (m,
1H), 7.59 (d, J = 8.8 Hz, 1H), 7.36 (d, J = 2.1 Hz, 1H), 7.34
(d, J = 2.4 Hz, 1H), 7.14 (d, J = 5.6 Hz, 1H), 6.98 (d, J =
2.0 Hz, 1H), 6.96 (d, J = 2.4 Hz, 1H), 5.04 (s, 2H), 3.90 (s,
3H), 3.78 (s, 3H). ESI-MS (m/z): 482.1, 484.1 ([M + H]+).
1-(3,5-difluorophenyl)-3-{4-[(4-methoxy-3,5-dimethylpyri-
din-2-yl)methoxy]phenyl}urea (7m) Yield 46.6% (white
solid). m.p.: 195–196 °C. IR(KBr, cm−1): υ 3421.1, 3298.0,
2922.4, 2852.2, 1642.2, 1606.0, 1563.1, 1510.0, 1477.3,
1444.9, 1383.8, 1292.2, 1234.4, 1202.5, 1159.0, 1118.3,
1102.0, 1002.1, 822.0, 671.3. 1H NMR (400 MHz,
1-(4-chlorophenyl)-3-{4-[(3,4-dimethoxypyridin-2-yl)meth-
oxy]phenyl}urea (7i) Yield 42.1% (yellow solid). m.p.:
197–198 °C. IR(KBr, cm−1): υ 3422.2, 2921.8, 2852.4,
1636.1, 1563.1, 1509.5, 1492.6, 1462.8, 1399.6, 1384.3,