Molecules 2012, 17
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3-Bromo-1-(3-chloropyridin-2-yl)-N-(4-ethoxyphenyl)-1H-pyrazole-5-carboxamide (7f). Yield: 90.9%.
White solid, m.p. 191–193 °C; 1H-NMR (CDCl3, 400 MHz) δ: 1.39 (t, 3H, J = 6.8 Hz, CH3), 3.98 (q, 2H,
J = 6.8 Hz, CH2), 6.79–6.81 (m, 2H, Ar-H), 6.84 (s, 1H, pyrazolyl-H), 7.31–7.33 (m, 2H, Ar-H), 7.41
(dd, J = 4.4, 8.0 Hz, 1H, pyridyl-H), 7.91 (dd, J = 1.6, 8.0 Hz, 1H, pyridyl-H), 8.15 (br. s, NH), 8.46 (dd,
1H, J = 1.6, 4.8 Hz, pyridyl-H); Elemental anal. (%), calcd. for C17H14BrClN4O2: C, 48.42; H, 3.35; N,
13.29; found: C, 48.66; H, 3.20; N, 12.91.
3-Bromo-N-(3-chloro-4-fluorophenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (7g). Yield:
1
95.3%. White solid, m.p. 167–169 °C; H-NMR (CDCl3, 400 MHz) δ: 6.85 (s, 1H, pyrazolyl-H),
7.02–7.07 (m, 2H, Ar-H), 7.20–7.23 (m, 2H, Ar-H), 7.45 (dd, J = 4.8, 7.6 Hz, 1H, pyridyl-H), 7.63 (dd,
1H, J = 1.6, 5.6 Hz, pyridyl-H), 7.95 (d, 1H, J = 8.0 Hz, pyridyl-H), 8.35 (br. s, NH); Elemental anal.
(%), calcd. for C15H8BrCl2FN4O: C, 41.89; H, 1.87; N, 13.03; found: C, 41.63; H, 2.17; N, 12.74.
3-Bromo-1-(3-chloropyridin-2-yl)-N-(2,4-dimethylphenyl)-1H-pyrazole-5-carboxamide (7h). Yield:
69.1%. White solid, m.p. 168–170 °C; 1H-NMR (CDCl3, 400 MHz) δ: 2.20 (s, 3H, CH3), 2.27 (s, 3H,
CH3), 6.85 (s, 1H, pyrazolyl-H), 6.96–7.00 (m, 2H, Ar-H), 7.39 (dd, 1H, J = 4.8, 8.0 Hz, pyridyl-H),
7.46 (d, 1H, J = 8.0 Hz, Ar-H), 7.66 (br. s, 1H, NH), 7.87 (dd, 1H, J = 1.2, 8.0 Hz, pyridyl-H), 8.46
(dd, 1H, J = 1.6, 4.8 Hz, pyridyl-H; Elemental anal. (%), calcd. for C17H14BrClN4O: C, 50.33; H, 3.48;
N, 13.81; found: C, 50.63; H, 3.50; N, 13.75.
3-Bromo-1-(3-chloropyridin-2-yl)-N-(2-methyl-4-nitrophenyl)-1H-pyrazole-5-carboxamide (7i). Yield:
1
62.3%. Yellow solid, m.p. 185–187 °C; H-NMR (DMSO-d6, 400 MHz) δ: 2.35 (s, 3H, CH3), 7.49 (s,
1H, Het-H), 7.61–7.67 (m, 2H, Ar-H), 8.06 (dd, J = 4.2 Hz, J = 4.4 Hz, 1H, Ar-H), 8.17 (d, J = 3.8 Hz,
1H, Py-H), 8.22 (d, J = 4.8 Hz, 1H, Py-H), 8.53 (dd, J = 4.5 Hz, J = 1.5 Hz, 1H, Py-H), 10.57(s, 1H,
NH); Elemental anal. (%), calcd. for C16H11BrClN5O3: C, 44.01; H, 2.54; N, 16.04; found: C, 44.23; H,
2.38; N, 15.89.
3-Bromo-1-(3-chloropyridin-2-yl)-N-(2,6-dimethylphenyl)-1H-pyrazole-5-carboxamide (7j). Yield:
1
49.5%. White solid, m.p. 216–219 °C; H-NMR (CDCl3, 400 MHz) δ: 2.21 (s, 6H, CH3), 6.93 (s, 1H,
pyrazolyl-H), 7.05–7.13 (m, 3H, Ar-H), 7.36–7.39 (m, 1H, pyridyl-H, 1H, NH), 7.87 (d, 1H, J = 6.8 Hz,
pyridyl-H), 8.46 (d, 1H, J = 1.6, 4.4 Hz, pyridyl-H); Elemental anal. (%), calcd. for C17H14BrClN4O:
C, 50.33; H, 3.48; N, 13.81; found: C, 50.03; H, 3.48; N, 13.81.
3-Bromo-1-(3-chloropyridin-2-yl)-N-(2-methyl-6-nitrophenyl)-1H-pyrazole-5-carboxamide (7k). Yield:
1
64.3%. White solid, m.p. 143-145 °C; H-NMR (DMSO-d6, 400 MHz) δ: 2.27 (s, 3H, CH3), 7.39
(s, 1H, pyrazolyl-H), 7.45 (t, 1H, J = 7.6 Hz, Ar-H), 7.61 (dd, J = 4.8, 8.0 Hz, 1H, pyridyl-H), 7.65
(d, 1H, J = 7.6 Hz, Ar-H), 7.79 (d, 1H, J = 7.6 Hz, Ar-H), 8.18 (dd, J = 1.2, 8.0 Hz, 1H, pyridyl-H),
8.50 (dd, 1H, J = 1.2, 4.4 Hz, 1H, pyridyl-H), 10.63 (br. s, NH); Elemental anal. (%), calcd. for
C16H11BrClN5O3: C, 44.01; H, 2.54; N, 16.04; found: C, 44.25; H, 2.69; N, 15.85.
3-Bromo-N-(2-chloro-4-nitrophenyl)-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (7l). Yield:
52.7%. White solid, m.p. 176–177 °C; 1H-NMR (CDCl3, 400 MHz) δ: 6.99 (s, 1H, pyrazolyl-H), 7.48
(dd, J = 4.8, 8.4 Hz, 1H, pyridyl-H), 7.96 (dd, J = 1.6, 8.4 Hz, 1H, pyridyl-H), 8.13 (dd, 1H, J = 2.4,