Med Chem Res
N-(2-aminophenyl)-4-(3-(3-(trifluoromethyl)phenyl)ureido)
benzamide (5a)
1610, 1548, 1317, 1234, 1087, 825, 755, 688; MS m/z:
379.8 [M−H]+.
White solid, yield: 62.6%; Mp: 216–218°C; 1H NMR (300
MHz, DMSO-d6) δ: 9.58 (s, 1H, –CONH–), 9.08 (s, 1H,
–NHCONH–), 9.05 (s, 1H, –NHCONH–), 7.96 (d, J = 8.4
Hz, 2H, Ar–H), 7.73 (s, 1H, Ar–H), 7.60–7.49 (m, 2H,
Ar–H), 7.37–7.30 (t, J = 8.1 Hz, 2H, Ar–H), 7.17 (d, J =
7.7 Hz, 1H, Ar–H), 7.04–6.93 (m, 2H, Ar–H), 6.78 (d, J =
7.8 Hz, 1H, Ar–H), 6.59 (t, J = 7.5 Hz, 1H, Ar–H), 4.88 (s,
2H, –NH2); 13C NMR (300 MHz, DMSO-d6) δ: 169.2
(ArCONH), 153.3 (NHCONH), 143.5 (C-2″), 141.0 (C-4),
136.2 (C-1′), 131.5 (C-3′), 129.1 (C-1), 129.0 (C-2, C-6),
128.8 (C-5′), 127.1 (C-6″), 126.7 (C-4″), 125.9 (C-2′), 124.8
(C-6′), 124.6 (CF3), 123.7 (C-1”), 121.9 (C-3, C-5), 120.7
(C-4′), 116.6 (C-5″), 116.4 (C-3″); IR (KBr cm−1) 3296,
1675, 1501, 1447, 1336, 1231, 1167, 1125, 1072, 883, 800,
746; MS m/z: 437.4 [M + Na]+.
N-(2-aminophenyl)-4-(3-(4-methoxyphenyl)ureido)
benzamide (5d)
White solid, yield: 70.9%; Mp: 216–218°C;1H NMR (300
MHz, DMSO-d6) δ: 9.53 (s, 1H, –CONH–), 9.20 (s, 1H,
–NHCONH–), 8.87 (s, 1H, –NHCONH–), 7.93 (t, J = 8.64
Hz, 2H, Ar–H), 7.57 (d, J = 8.7 Hz, 2H, Ar–H), 7.38 (d, J
= 8.9 Hz, 2H, Ar–H), 7.16 (d, J = 7.7 Hz, 1H, Ar–H),
6.96–6.77 (m, 4H, Ar–H), 6.60 (m, 1H, Ar–H), 4.87 (s, 2H,
–NH2), 3.72 (s, 3H, –OCH3); 13C NMR (300 MHz, DMSO-
d6) δ: 169.4 (ArCONH), 159.2 (C-4′), 153.6 (NHCONH),
143.5 (C-2″), 141.1 (C-4), 132.5 (C-1′), 129.2 (C-1), 129.0
(C-2, C-6), 127.0 (C-6″), 126.8 (C-4″), 123.8 (C-1″), 122.0
(C-3, C-5), 119.9 (C-2′, C-6′), 116.6 (C-5″), 116.4 (C-3”),
114.7 (C-3′, C-5′), 56.4 (OCH3); IR (KBr cm−1) 3228,
1696, 1610, 1509, 1318, 1233, 827, 752, 690; MS m/z:
399.4 [M + Na]+.
N-(2-aminophenyl)-4-(3-(4-(trifluoromethyl)phenyl)ureido)
benzamide (5b)
N-(2-aminophenyl)-4-(3-(3-chloro-4-fluorophenyl)ureido)
benzamide (5e)
1
White solid, yield 63.1%; Mp: 234–236°C; H NMR (300
MHz, DMSO-d6) δ: 9.53 (s, 1H, –CONH–), 9.33 (s, 1H,
–NHCONH–), 8.04 (s, 1H, –NHCONH–), 7.94 (d, J = 8.0
Hz, 2H, Ar–H), 7.69–7.59 (m, 3H, Ar–H), 7.41 (d, J = 8.0
Hz, 2H, Ar–H), 7.14 (d, J = 7.5 Hz, 1H, Ar–H), 7.00–6.85
(m, 2H, Ar–H), 6.79 (d, J = 7.4 Hz, 1H, Ar–H), 6.60 (t, J =
7.6 Hz, 1H, Ar–H), 4.87 (s, 2H, –NH2); 13C NMR (300
MHz, DMSO-d6) δ: 169.2 (ArCONH), 154.4 (NHCONH),
143.5 (C-2″), 141.0 (C-4), 137.2 (C-1′), 135.8 (C-4′), 129.1
(C-1), 129.0 (C-2, C-6), 127.1 (C-6″), 126.1 (C-4″), 125.7
(C-3′, C-5′), 124.8 (CF3), 123.8 (C-1″), 121.9 (C-3, C-5),
121.7 (C-2′, C-6′), 116.6 (C-5″), 116.5 (C-3″); IR (KBr
cm−1) 3329, 1702, 1603, 1547, 1410, 1317, 1240, 1181,
1112, 1069, 841, 756; MS m/z: 453.4 [M + Na]+.
White solid, yield: 67.5%; Mp: 204–206°C;1H NMR (300
MHz, DMSO-d6) δ: 9.50 (s, 1H, –CONH–), 9.02 (s, 1H,
–NHCONH–), 9.00 (s, 1H, –NHCONH–), 7.94–7.84 (m,
3H, Ar–H), 7.62 (d, J = 8.7 Hz, 2H, Ar–H), 7.48–7.30 (m,
2H, Ar–H), 7.16 (d, J = 6.8 Hz, 1H), 6.96 (t, J = 8.0 Hz,
1H, Ar–H), 6.78 (d, J = 7.9 Hz, 1H, Ar–H), 6.60 (t, J = 7.7
Hz, 1H, Ar–H), 4.87 (s, 2H, –NH2); 13C NMR (300 MHz,
DMSO-d6) δ: 169.2 (ArCONH), 158.8 (C-4′), 153.6
(NHCONH), 143.5 (C-2″), 141.9 (C-4), 135.2 (C-1′), 129.1
(C-1), 129.0 (C-2, C-6), 127.0 (C-6″), 126.7 (C-4″), 124.7
(C-6′), 123.9 (C-2′), 123.7 (C-1″), 121.5 (C-3, C-5), 121.0
(C-3′), 116.6 (C-5″), 116.4 (C-3″), 113.9 (C-5′); IR (KBr
cm−1) 3331, 1698, 1610, 1317, 1245, 1085, 678; MS m/z:
397.8 [M−H]+.
N-(2-aminophenyl)-4-(3-(4-chlorophenyl)ureido)benzamide
(5c)
N-(2-aminophenyl)-4-(3-benzylureido)benzamide (5f)
White solid, yield: 64.3%; Mp: 233–235°C;1H NMR (300
MHz, DMSO-d6) δ: 9.54 (s, 1H, –CONH–), 9.02 (s, 1H,
–NHCONH–), 8.93 (s, 1H, –NHCONH–), 7.94 (d, 2H,
Ar–H), 7.54–7.49 (m, 4H, Ar–H), 7.34 (d, 2H, Ar–H), 7.16
(d, J = 15.0 Hz, 1H, Ar–H), 6.97 (t, J = 7.83 Hz, 1H,
Ar–H), 6.78 (d, J = 7.8 Hz, 1H, Ar–H), 6.60 (t, J = 7.6 Hz,
1H, Ar–H), 4.87 (s, 2H, –NH2); 13C NMR (300 MHz,
DMSO-d6) δ: 169.2 (ArCONH), 153.9 (NHCONH), 143.5
(C-2″), 141.0 (C-4), 137.7 (C-1′), 134.8 (C-4′), 129.2 (C-1),
129.1 (C-2, C-6), 129.0 (C-3′, C-5′), 127.0 (C-6”), 126.7 (C-
4″), 123.8 (C-1″), 121.9 (C-3, C-5), 121.0 (C-2′, C-6′),
116.6 (C-5″), 116.4 (C-3”); IR (KBr cm−1) 3326, 1698,
White solid, yield: 68.2%; Mp: 241–243°C; 1H NMR (300
MHz, DMSO-d6) δ: 9.99 (s, 1H, –CONH–), 9.12 (s, 1H,
–NHCONH–), 9.07 (s, 1H, –NHCONH–), 8.13 (s, 1H,
Ar–H), 7.95 (d, J = 8.6 Hz, 2H, Ar–H), 7.68–7.60 (m, 4H,
Ar–H), 7.16 (d, J = 7.4 Hz, 2H, Ar–H), 6.97 (t, J = 7.9 Hz,
2H, Ar–H), 6.78 (d, J = 7.6 Hz, 1H, Ar–H), 6.60 (t, J = 7.6
Hz, 1H, Ar–H), 4.87 (s, 2H, –NH2), 4.25 (s, 2H, –CH2–);
13C NMR (300 MHz, DMSO-d6) δ: 169.2 (ArCONH),
153.3 (NHCONH), 143.5 (C-2”), 141.0 (C-4), 137.9 (C-1′),
129.1 (C-1), 129.0 (C-2, C-6), 128.5 (C-3′, C-5′), 126.8 (C-
2′, C-6′), 126.7 (C-4′, C-4”), 123.8 (C-1″), 121.9 (C-3, C-5),
116.6 (C-5″), 116.4 (C-3″), 44.8 (CH2); IR (KBr cm−1
)