Medicinal Chemistry Research
2H), 6.95 (d, J 9.0 Hz, 2H), 6.67 (s, 1H), 3.83 (s, 3H), 2.9
(q, J 7.1 Hz, 2H), 0.99 (t, J 7.1 Hz, 3H); 13C NMR
(100 MHz, CDCl3): δ 157.24, 150.32, 141.71, 138.54,
134.63, 128.21, 124.73, 114.50, 115.23, 110.54, 102.12,
56.90, 32.11, 14.62; GCMS: m/z calcd for C18H17BrN2OS
389.31, found 390 (M+).
(m, 1H), 1.48 (m, 2H), 1.52 (m, 2H), 1.33 (m, 2H) 1.09 (t, J
7.1 Hz, 3H), 0.96 (t, J 7.1 Hz, 3H); 13C NMR (100 MHz,
CDCl3): δ 157.24, 150.32, 141.71, 138.54, 134.63, 128.21,
124.73, 114.50, 115.23, 110.54, 102.12, 62.52, 56.90,
32.11, 25.23, 18.03, 14.62, 9.62; GCMS: m/z calcd for
C24H29BrN2OS 473.47, found 474 (M+).
4-(4-bromophenyl)-N-isopropyl-N-(4-methoxyphenyl)
thiazol-2-amine (3g)
N-ethyl-N-(4-methoxyphenyl)-4-(4-nitrophenyl)thiazol-2-
amine (3k)
Yellow solid; Yield: 90%; m.p. 122–124 °C; FT-IR (cm−1):
1395, 1606, 1564, 725; 1H NMR (400 MHz, CDCl3): δ 7.66
(d, J 8.6 Hz, 2H), 7.56 (d, J 8.6 Hz, 2H), 7.31 (d, J 9.0 Hz,
2H), 6.95 (d, J 9.0 Hz, 2H), 6.67 (s, 1H), 3.83 (s, 3H), 2.04
(m, 1H), 1.22 (d, J 6.7 Hz, 6H); 13C NMR (100 MHz,
CDCl3): δ 157.24, 150.32, 141.71, 138.54, 134.63, 128.21,
124.73, 114.50, 115.23, 110.54, 102.12, 56.90, 32.11,
14.62; GCMS: m/z calcd for C19H19BrN2OS 403.34, found
404 (M+).
Orange red solid; Yield: 90%; m.p. 86–88 °C; FT-IR
(cm−1): 1340, 1592, 1547, 1347, 1505; 1H NMR (400 MHz,
CDCl3): δ 8.21 (d, J 8.9 Hz, 2H), 7.97 (d, J 8.9 Hz, 2H),
7.27 (d, J 8.9 Hz, 2H), 6.97 (d, J 8.9 Hz, 2H), 6.81 (s,1H),
3.94 (q, 7.1 Hz, 2H), 3.84 (s, 3H), 1.01 (t, J 7.4 Hz, 3H);
13C NMR (100 MHz, CDCl3): δ 171.40, 159.08, 149.39,
146.74, 141.34, 137.60, 129.13, 126.38, 124.07, 115.34,
105.33, 55.59, 54.68, 11.47; GCMS: m/z calcd for
C18H17N3O3S 355.41, found 355 (M+).
4-(4-bromophenyl)-N-(4-methoxyphenyl)-N-propylthiazol-
2-amine (3h)
N-isopropyl-N-(4-methoxyphenyl)-4-(4-nitrophenyl)thiazol-
2-amine (3l)
Yellow solid; Yield: 94%; m.p. 118–120 °C; FT-IR (cm−1):
1395, 1610, 1564, 725; 1H NMR (400 MHz, CDCl3): δ 7.71
(d, J 8.5 Hz, 2H), 7.48 (d, J 8.5 Hz, 2H), 7.27 (d, J 7.2 Hz,
2H), 6.96 (d, J 8.8 Hz, 2H), 6.59 (s, 1H), 3.93 (t, J 7.5 Hz,
2H), 3.84 (s, 3H), 1.71 (m, 2H), 0.95 (t, J 7.5 Hz, 3H); 13C
NMR (100 MHz, CDCl3): δ 171.41, 158.71, 150.36,
147.07, 137.73, 131.50, 129.38, 127.82, 121.10, 115.37,
101.69, 55.72, 54.66, 20.98, 11.40; GCMS: m/z calcd for
C19H19BrN2OS 403.34, found 404 (M+).
Orange red solid; Yield: 88%; m.p. 80–82 °C; FT-IR
(cm−1): 1335, 1593, 1531, 1331, 1505; 1H NMR (400 MHz,
CDCl3): δ 8.21 (d, J 8.9 Hz, 2H), 7.97 (d, J 8.9 Hz, 2H),
7.27 (d, J 8.9 Hz, 2H), 6.97 (d, J 8.9 Hz, 2H), 6.81 (s,1H),
3.84 (s, 3H), 3.94 (m, 1H), 1.01 (d, J 7.1 Hz, 6H); 13C NMR
(100 MHz, CDCl3): δ 171.52, 159.25, 149.46, 146.36,
140.95, 137.46, 129.16, 126.41, 124.14, 115.40, 105.12,
55.74, 50.47, 21.20; GCMS: m/z calcd for C19H19N3O3S
369.44, found 369 (M+).
N-sec-butyl-4-(4-bromophenyl)-N-(4-methoxyphenyl)
thiazol-2-amine (3i)
N-(4-methoxyphenyl)-4-(4-nitrophenyl)-N-propylthiazol-2-
amine (3m)
Yellow solid; Yield: 94%; m.p. 114–116 °C; FT-IR (cm−1):
1395, 1608, 1565, 725; 1H NMR (400 MHz, CDCl3): δ 7.66
(d, J 8.4 Hz, 2H), 7.50 (d, J 8.4 Hz, 2H), 7.29 (d, J 7.2 Hz,
2H), 6.91 (d, J 8.8 Hz, 2H), 6.69 (s, 1H), 3.81 (s, 3H), 1.69
(m, 1H), 1.20 (m, 2H), 1.01 (d, J 6.6 Hz, 3H), 0.86 (t, J
6.7 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 164.64,
149.09, 138.38, 131.98, 130.40, 129.55, 128.59, 127.62,
122.31, 119.79, 102.27, 57.93, 28.28, 18.91, 11.70; GCMS:
m/z calcd for C20H21BrN2OS 417.36 found 418 (M+).
Orange red solid; Yield: 90%; m.p. 76–78 °C; FT-IR
(cm−1): 1332, 1593, 1536, 1336, 1504; 1H NMR (400 MHz,
CDCl3): δ 8.21 (d, J 8.9 Hz, 2H), 7.97 (d, J 8.9 Hz, 2H),
7.27 (d, J 8.9 Hz, 2H), 6.97 (d, J 8.9 Hz, 2H), 6.81 (s,1H),
3.94 (t, J 7.1 Hz, 2H), 3.84 (s, 3H), 1.71 (m, 2H), 0.97 (t, J
7.4 Hz, 3H); (100 MHz, CDCl3): δ 171.52, 159.25, 149.46,
146.36, 140.95, 137.46, 129.16, 126.41, 124.14, 115.40,
105.12, 55.74, 54.47, 21.19, 11.39; GCMS: m/z calcd for
C19H19N3O3S 369.44, found 369 (M+).
4-(4-bromophenyl)-N-(4-methoxyphenyl)-N-(octan-3-yl)
thiazol-2-amine (3j)
N-sec-butyl-N-(4-methoxyphenyl)-4-(4-nitrophenyl)thiazol-
2-amine (3n)
Yellow solid; Yield: 92%; m.p. 110–112 °C; FT-IR (cm−1):
1390, 1610, 1565, 730; 1H NMR (400 MHz, CDCl3): δ 7.66
(d, J 8.9 Hz, 2H), 7.49 (d, J 8.9 Hz, 2H), 7.32 (d, J 8.7 Hz,
2H), 6.93 (d, J 8.7 Hz, 2H), 6.48 (s, 1H), 3.86 (s, 3H), 2.92
Orange red solid; Yield: 94%; m.p. 72–74 °C; FT-IR
(cm−1): 1335, 1593, 1531, 1331, 1505; 1H NMR (400 MHz,
CDCl3): δ 8.21 (d, J 8.9 Hz, 2H), 7.97 (d, J 8.9 Hz, 2H),
7.27 (d, J 8.9 Hz, 2H), 6.97 (d, J 8.9 Hz, 2H), 6.81 (s,1H),