J = 8.6 Hz, 2H), 7.71 (d, J = 8.7 Hz, 2H), 7.41 (dd, J = 9.0, 5.0 Hz, 2H), 7.06 (t, J = 8.9 Hz,
13
2H), 6.62 (t, J = 5.5 Hz, 1H, NH), 5.37 (s, 2H, -CH2-), 4.37 (d, J = 5.6 Hz, 2H, NCH2). C
NMR (101 MHz, DMSO): δ 165.49, 158.54, 156.21, 155.61, 145.93, 142.45, 137.21, 126.73,
126.69, 126.09, 124.83, 124.37, 124.05, 123.39, 119.79, 119.72, 119.63, 115.66, 115.44,
52.63, 35.33. HRMS: m/z (M + H)+ cacld. for C19H17F4N6O2: 437.1349 found: 437.1363.
4.4.3.7.
2-{4-[3-(4-Chloro-phenyl)-ureidomethyl]-[1,2,3]triazol-1-yl}-N-(2-fluoro-
phenyl)-acetamide (4g). Yield 87%, White solid; mp 277-279 °C; IR (KBr, νmax /cm-1): 3356
(NH str), 3258 (NH str), 3130 (C-H str, triazole), 1666 (C=O str), 1661 (C=O str), 1597, 1555,
1
1491, 1458, 1317, 1061, 972, 817, 752, 698, 637. H NMR (400 MHz, DMSO): δ 10.28 (s,
1H, NH), 8.74 (s, 1H, NH), 7.99 (s, 1H, triazolyl-H), 7.91 (t, J = 8.7 Hz, 1H), 7.44 (d, J = 8.8
Hz, 2H), 7.28 (t, J = 7.6 Hz, 3H), 7.20 – 7.15 (m, 2H), 6.67 (t, J = 5.5 Hz, 1H, NH), 5.40 (s,
2H, -CH2-), 4.37 (d, J = 5.5 Hz, 2H, NCH2). 13C NMR (101 MHz, DMSO): δ 165.34, 155.40,
155.13, 152.69, 145.75, 139.85, 128.93, 126.15, 126.08, 126.00, 125.88, 125.06, 124.98,
124.94, 124.83, 124.21, 119.63, 116.16, 115.97, 52.37, 35.32. HRMS: m/z (M + H)+ cacld. for
C18H17ClFN6O2: 403.1086 found: 403.1326.
4.4.3.8.
2-{4-[3-(4-Chloro-phenyl)-ureidomethyl]-[1,2,3]triazol-1-yl}-N-(3-fluoro-
phenyl)-acetamide (4h). Yield 83%, White solid; mp 290-292 °C; IR (KBr, νmax /cm-1): 3345
(NH str), 3302 (NH str), 3102 (C-H str, triazole), 1697 (C=O str), 1670 (C=O str), 1599, 1555,
1
1491, 1447, 1343, 1059, 972, 868, 819, 783, 731, 706, 682, 640, 606. H NMR (400 MHz,
DMSO): δ 10.67 (s, 1H, NH), 8.74 (s, 1H, NH), 8.00 (s, 1H, triazolyl-H), 7.56 (dt, J = 11.6,
2.1 Hz, 1H), 7.46 – 7.42 (m, 2H), 7.41 – 7.35 (m, 1H), 7.32 – 7.25 (m, 3H), 6.93 (td, J = 8.3,
1.9 Hz, 1H), 6.67 (t, J = 5.6 Hz, 1H, NH), 5.33 (s, 2H, -CH2-), 4.37 (d, J = 5.6 Hz, 2H,
13
NCH2). C NMR (101 MHz, DMSO): δ 165.17, 163.79, 161.39, 155.40, 145.78, 140.62,
140.51, 139.85, 131.12, 131.06, 128.93, 125.06, 124.81, 119.64, 115.46, 115.44, 110.83,
110.62, 106.65, 106.39, 52.59, 35.32. HRMS: m/z (M + H)+ cacld. for C18H17ClFN6O2:
403.1086 found: 403.1326.
4.4.3.9.
2-{4-[3-(4-Chloro-phenyl)-ureidomethyl]-[1,2,3]triazol-1-yl}-N-(4-fluoro-
phenyl)-acetamide (4i). Yield 90%, White solid; mp 248-250 °C; IR (KBr, νmax /cm-1): 3329
(NH str), 3271 (NH str), 3140 (C-H str, triazole), 1672 (C=O str), 1663 (C=O str), 1597, 1557,
1
1510, 1470, 1300, 1055, 837, 820, 729, 642. H NMR (400 MHz, DMSO): δ 10.51 (s, 1H,
NH), 8.74 (s, 1H, NH), 7.99 (s, 1H, triazolyl-H), 7.59 (dd, J = 9.0, 5.0 Hz, 2H), 7.43 (d, J =