Med Chem Res (2014) 23:2667–2675
2673
Ar), 8.1 (s, 1H, Ar). 13C NMR (CDCl3, 400 MHz): d
169.97 (C=O), 162.62 (C-2), 152.06 (C-4), 144.38 (C-7),
142.51 (C-100), 138.94 (C-50), 137.09 (C-15), 134.69 (C-
30), 130.00 (C-120, 140), 128.46 (CH-9, 11), 127.99 (CH-17,
19), 127.72 (CH-18), 127.62 (CH-16, 20), 127.56 (CH-
130), 127.44 (CH-110, 150), 126.92 (CH-8, 12), 124.30 (CH-
10), 115.79 (C-5), 105.12 (C-50), 60.21 (CH2-80), 47.47
(CH2-13), 14.19 (CH3-90), 13.07 (CH3-14). MS: m/z [M?]
495.2. Anal. calcd. for C29H26N4O2S: C, 70.42; H, 5.30;
N, 11.33. Found: C, 70.40; H, 5.250; N, 11.30.
CH3), 3.97 (q, 1H, CH), 4.13 (q, 1H, CH), 4.30 (q, 2H,
CH2), 6.85 (d, 1H, Ar), 6.93–6.95 (m, 2H, Ar), 7.05–7.09
(m, 2H, Ar), 7.18 (s, 1H, Ar), 7.22 (s, 1H, Ar), 7.36–7.51
(m, 5H, Ar), 7.95 (s, 1H, Ar), 7.97 (d, 1H, Ar), 8.56 (s, 1H,
Ar). 13C NMR (CDCl3, 400 MHz): d 172.81 (C=O), 161.85
(C-2), 153.27 (C-4), 145.94 (C-130), 144.45 (C-7), 143.93
(C-100), 139.18 (C-110), 134.19 (C-130), 130.50 (C140),
130.15 (9, 12), 128.41 (CH-17, 19), 128.28 (CH-18),
128.17 (CH-16, 20), 127.84 (CH-10), 127.15 (CH-8, 12),
126.78 (CH-150), 119.70 (C-120), 115.3 (C-4),103.46 (C-
50), 60.69 (CH2-80), 47.74 (CH2-13), 14.15 (CH3-90), 12.87
(CH3-14). MS: m/z [M?] 584.8. Anal. calcd. for
C29H24N6O6S: C, 59.58; H, 4.14; N, 14.38. Found: C,
59.55; H, 4.12; N, 14.33.
3-[2-(Ethyl-phenyl-amino)-4-phenyl-thiazol-5-yl]-1-(4-flu-
oro-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester
(4h) This compound was obtained as yellow solid, yield
213 mg (82 %), mp 159–160 °C. IR (KBr): 1,714 (C=O).
1H NMR (CDCl3, 400 MHz): d 1.2 (t, 3H, CH3), 1.3 (t, 3H,
CH3), 4.1 (q, 2H, CH2), 4.15 (q, 2H, CH2), 6.82 (d, 2H,
Ar), 7.04–7.07 (m, 2H, Ar), 7.10–7.15 (m, 3H, Ar), 7.27 (s,
1H, Ar), 7.35–7.49 (m, 4H, Ar), 8.12 (s, 1H, Ar). 13C NMR
(CDCl3, 400 MHz): d 170.14 (C=O), 162.56 (C-2), 160.42
(C-130), 152.14 (C-4), 144.29 (C-7), 142.55 (C-50), 137.23
(C-15), 135.02 (C-100), 134.99 (C-30), 130.66 (C-9, 11),
128.07 (CH-17, 19), 127.75 (CH-18), 127.72 (CH-16, 20),
127.58 (CH-10), 127.01 (CH-8, 12), 126.18 (CH-110),
126.09 (CH-150), 115.78 (CH-120, 150), 115.45 (C-5), 104.
80 (C-40), 60.31 (CH2-80), 47.48 (CH2-13), 14.21 (CH3-90),
13.10 (CH3-14). MS: m/z [M?] 513.0. Anal. calcd. for
C29H26FN4O2S: C, 67.95; H, 4.92; N, 10.93. Found: C,
67.90; H, 4.89; N, 10.90.
3-[2-(Benzyl-phenyl-amino)-4-phenyl-thiazol-5-yl]-1H-
pyrazole-4-carboxylic acid ethyl ester (4k) This com-
pound was obtained as yellow solid, yield 168 mg (80 %),
mp 148–149 °C. IR (KBr): 1,716 (C=O). 1H NMR (CDCl3,
400 MHz): d 1.2 (t, 3H, CH3), 1.21 (t, 3H, CH2), 4.14 (q,
2H, CH2), 5.2 (s, 2H, CH2), 7.25 (d, 3H, Ar), 7.27–7.34 (m,
10H, Ar), 7.49 (d, 2H, Ar), 7.97 (s, 1H, Ar). 13C NMR
(CDCl3, 400 MHz): d 170.14 (C=O), 162.62 (C-2), 151.95
(C-42), 144.37 (C-7), 142.47 (C-14), 130.02 (C-30), 128.49
(CH-50), 128.46 (CH-9, 11), 128.44 (CH-22, 24), 128.39
(CH-23), 128.3 (CH-15, 19), 127.66 (CH-21, 25), 127.46
(CH-16, 18), 126.83 (CH-17), 112.87 (C-5), 105.71 (C-40)
60.26 (CH2-13), 56.35 (CH2-80), 14.14 (CH3-90). MS: m/
z [M?] 481.0. Anal. calcd. for C28H24N4O2S: C, 69.98; H,
5.03; N, 11.66. Found: C, 69.95; H, 5.01; N, 11.61.
1-(4-Chloro-phenyl)-3-[2-(ethyl-phenyl-amino)-4-phenyl-
thiazol-5-yl]-1H-pyrazole-4-carboxylic acid ethyl ester
(4i) This compound was obtained as yellow solid, yield
215 mg (80 %), mp 172–173 °C. IR (KBr): 1,701 (C=O).
1H NMR (CDCl3, 400 MHz): d 1.2 (t, 3H, CH3), 1.3 (t, 3H,
CH3), 4.1 (q, 2H, CH2), 4.15 (q, 2H, CH2), 6.80 (d, 2H,
Ar), 7.03–7.05 (m, 2H, Ar), 7.09–7.15 (m, 5H, Ar), 7.16 (s,
1H, Ar), 7.26–7.49 (m, 4H, Ar), 8.12 (s, 1H, Ar). 13C NMR
(CDCl3, 400 MHz): d 170.2 (C=O), 162.48 (C-2), 152.23
(C-4), 144.27 (C-7), 142.72 (C-50), 137.43 (C-100), 134.62
(C-30), 133.38 (C-15), 130.06 (C-130), 128.56 (CH-9, 11),
127.77 (CH-17, 19), 127.72 (CH-120, 140), 127.02 (CH-18),
125.47 (CH-15, 20), 120.3 (110, 150), 115.98 (C-5), 104.72
(C-40), 60.31 (CH2-80), 47.48 (CH2-13), 14.19 (CH3-90),
13.1 (CH3-14). MS: m/z [M ? 1] 530.0. Anal. calcd. for
C29H26FN4O2S: C, 65.84; H, 4.76; N, 10.59. Found: C,
65.81; H, 4.72; N, 10.55.
3-[2-(Benzyl-phenyl-amino)-4-phenyl-thiazol-5-yl]-1-phenyl-
1H-pyrazole-4-carboxylic acid ethyl ester (4l) This com-
pound was obtained as yellow solid, yield 202 mg (83 %),
mp 152–153 °C. IR (KBr): 1,715 (C=O). 1H NMR (CDCl3,
400 MHz): d 1.2 (t, 3H, CH3), 1.21 (t, 3H, CH2), 4.14 (q,
2H, CH2), 5.23 (d, 1H, CH), 6.91 (d, 1H, CH), 6.89 (d, 2H,
Ar), 6.91–7.19 (m, 8H, Ar), 7.25–7.38 (m, 11H, Ar), 8.1 (s,
1H, Ar). 13C NMR (CDCl3, 400 MHz): d 170.19 (C=O),
162.59 (C-2), 151.95 (C-4), 144.47 (C-7), 142.48 (C-50),
138.81 (C-100), 137.55 (C-14), 136.90 (C-20), 134.45 (C-
30), 129.83 (C-120, 140), 128.37 (C-9, 11), 128.33 (C-22,
24), 128.07 (CH-23), 127.95 (CH-16, 18), 127.64 (CH-15,
17), 127.53 (CH-21, 25), 127.29 (CH-10), 126.33 (CH-16),
124.21 (C-110, 150), 115.71 (C-5), 105.71 (C-40), 60.21
(CH2-13), 56.12 (CH2-80), 14.12 (CH3-90). MS: m/z [M?]
557.0. Anal. calcd. for C34H28N4O2S: C, 73.36; H, 5.07;
N, 10.06. Found: C, 73.31; H, 5.02; N, 10.04.
1-(2,4-Dinitro-phenyl)-3-[2-(ethyl-phenyl-amino)-4-phenyl-
thiazol-5-yl]-1H-pyrazole-4-carboxylic acid ethyl ester
(4j) This compound was obtained as orange solid, yield
222 mg (75 %), mp 185–186 °C. IR (KBr): 1,712 (C=O).
1H NMR (CDCl3, 400 MHz): d 1.2 (t, 3H, CH3), 1.3 (t, 3H,
3-[2-(Benzyl-phenyl-amino)-4-phenyl-thiazol-5-yl]-1-(4-
fluoro-phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester
(4m) This compound was obtained as yellow solid, yield
206 mg (82 %), mp 175–176 °C. IR (KBr): 1,709 (C=O).
123