129.48, 125.85, 125.13, 122.63, 107.05, 26.53, 18.11. Anal. calcd
for C20H14Cl3F3N4O2: C, 47.50; H, 2.79; N, 11.08; found: C,
47.56; H, 2.78; N, 11.14.
NHCH3), 2.18 (s, 3H, Ph-CH3). 13C NMR (101 MHz, DMSO-d6)
ꢁ 166.13, 155.59, 141.49, 139.79, 139.28, 138.72, 138.43,
137.05, 135.96, 131.46, 131.17, 131.15, 130.93, 130.48, 125.35,
120.81, 106.50, 92.28, 26.12, 17.64. Anal. calcd for
C20H14Cl2F3IN4O2: C, 40.23; H, 2.36; N, 9.38; found: C, 40.20;
H, 2.41; N, 9.50.
4.1.4.4. N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-
(2,6-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
ꢂꢉꢊꢌꢅꢆꢇꢈꢅ
carboxamide (7d). Yellow solid, yield 60.2%, mp 257
1H (400 MHz, DMSO-d6) ꢁ 10.37 (s, 1H, Ph-NH-CO), 8.27 (d, J
= 4.6 Hz, 1H, Ph-CO-NH), 7.80 (s, 1H, Ph-H), 7.67 (d, J = 1.1
Hz, 1H, Ph-H), 7.65 (s, 1H, Pyrazole-H), 7.62 – 7.57 (m, 1H, Ph-
H ), 7.48 (d, J = 2.2 Hz, 1H, Ph-H), 7.33 (d, J = 2.2 Hz, 1H, Ph-
H), 2.63 (d, J = 4.6 Hz, 3H, NHCH3), 2.16 (s, 3H, Ph-CH3). 13C
NMR (101 MHz, DMSO-d6) ꢁ 166.61, 155.72, 142.47, 139.67,
139.18, 136.74, 135.98, 133.21, 132.53, 131.81, 131.60, 131.49,
129.12, 125.77, 121.61, 120.74, 118.95, 106.91, 26.50, 18.05.
Anal. calcd for C20H14Cl3F3N4O2: C, 47.50; H, 2.79; N, 11.08;
found: C, 47.45; H, 2.90; N, 11.10.
4.1.4.9. N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-
(2-chloro-5-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
carboxamide (7i). White solid, yield 62.5%, mp 220ꢂꢉꢉꢃꢅꢆꢇꢈꢅ1H
NMR (400 MHz, DMSO-d6) ꢁ 10.36 (s, 1H, Ph-NH-CO), 8.33
(d, J = 4.5 Hz, 1H, Ph-CO-NH), 7.74 (s, 1H, Pyrazole-H), 7.73 –
7.66 (m, 2H, 2Ph-H), 7.51 – 7.43 (m, 2H, Ph-H), 7.36 (d, J = 1.9
Hz, 1H, Ph-H), 2.65 (d, J = 4.5 Hz, 3H, NHCH3), 2.18 (s, 3H,
Ph-CH3). 13C NMR (101 MHz, DMSO-d6) ꢁ 166.17, 161.51,
159.06, 155.57, 142.12, 139.35, 138.69, 138.43, 138.33, 135.94,
131.46, 131.22, 130.93, 126.14, 125.41, 124.80, 122.13, 106.51,
25.95, 17.55. Anal. calcd for C20H14Cl2F4N4O2: C, 49.10; H, 2.88;
N, 11.45; found: C, 49.19; H, 2.77; N, 11.61.
4.1.4.5. N-(4-bromo-2-methyl-6-(methylcarbamoyl)phenyl)-1-
(2,5-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
carboxamide (7e). Yellow solid, yield 63.7%, mp 263ꢂꢉꢋꢍꢅ ꢆꢇꢈꢅ
1H NMR (400 MHz, DMSO-d6) ꢁ 10.36 (s, 1H, Ph-NH-CO),
8.33 (d, J = 4.6 Hz, 1H, Ph-CO-NH), 7.87 (d, J = 2.1 Hz, 1H, Ph-
H), 7.75 (s, 1H, Pyrazole-H), 7.69 – 7.67 (m, 1H, Ph-H), 7.66 (d,
J = 2.1 Hz, 1H, Ph-H), 7.63 (d, J = 1.8 Hz, 1H, Ph-H), 7.48 (d, J
= 1.8 Hz, 1H, Ph-H), 2.65 (d, J = 4.5 Hz, 3H, NHCH3), 2.18 (s,
3H, Ph-CH3). 13C NMR (101 MHz, DMSO-d6) ꢁ 166.00, 155.49,
142.12, 139.32, 138.96, 138.43, 136.19, 134.15, 134.06, 131.88,
131.12, 130.87, 129.38, 129.00, 128.95, 128.24, 125.20, 106.52,
26.09, 17.56. Anal. calcd for C20H14BrCl2F3N4O2: C, 43.66; H,
2.56; N, 10.18; found: C, 43.72; H, 2.63; N, 10.23.
4.1.4.10. N-(4-bromo-2-methyl-6-(methylcarbamoyl)phenyl)-
1-(2-chloro-5-fluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
ꢂꢉꢃꢍꢅ ꢆꢇꢈꢅ
carboxamide (7j). Yellow solid, yield 69.2%, mp 213
1H NMR (400 MHz, DMSO-d6) ꢁ 10.36 (s, 1H, Ph-NH-CO),
8.33 (d, J = 4.5 Hz, 1H, Ph-CO-NH), 7.73 (s, 1H, Pyrazole-H),
7.70 – 7.65 (m, 2H, 2Ph-H), 7.56 – 7.50 (m, 2H, Ph-H), 7.48 (d, J
= 1.9 Hz, 1H, Ph-H), 2.65 (d, J = 4.5 Hz, 3H, NHCH3), 2.18 (s,
3H, Ph-CH3). 13C NMR (101 MHz, DMSO-d6) ꢁ 167.22, 162.51,
160.26, 156.70, 142.91, 140.45, 139.89, 139.46, 139.34, 136.93,
132.56, 132.42, 131.98, 127.24, 126.51, 125.85, 123.18, 107.76,
27.22, 18.72. Anal. calcd for C20H14BrClF4N4O2: C, 45.01; H,
2.64; N, 10.50; found: C, 45.10; H, 2.71; N, 10.55.
4.1.4.6. 1-(5-bromo-2-chlorophenyl)-N-(4-chloro-2-methyl-6-
(methylcarbamoyl)phenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
carboxamide (7f). Yellow solid, yield 62.4%, mp 257ꢂꢉꢊꢌꢅ ꢆꢇꢈꢅ
1H NMR (400 MHz, DMSO-d6) ꢁ 10.37 (s, 1H, Ph-NH-CO),
8.34 (d, J = 1.4 Hz, 1H, Ph-CO-NH), 7.97 (s, 1H, Ph-H), 7.73 –
7.77 (m, 2H, Pyrazole-H and Ph-H), 7.61 (d, J = 8.3 Hz, 1H, Ph-
H), 7.50 (s, 1H, Ph-H), 7.37 (s, 1H, Ph-H), 2.67 (s, 3H, NHCH3),
2.19 (s, 3H, Ph-CH3). 13C NMR (101 MHz, DMSO-d6) ꢁ 166.64,
156.07, 142.65, 139.81, 139.19, 139.09, 136.48, 134.51, 132.18,
131.94, 131.66, 131.61, 131.44, 130.44, 125.85, 125.11, 122.63,
107.04, 26.56, 18.11. Anal. calcd for C20H14BrCl2F3N4O2: C,
43.66; H, 2.56; N, 10.18; found: C, 43.71; H, 2.52; N, 10.13.
4.1.4.11. N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-
1-(2-chloro-5-(trifluoromethyl) phenyl)-3-(trifluoromethyl)-1H-
pyrazole-5-carboxamide (7k). Yellow solid, yield 62.0%, mp
ꢂꢉꢏꢉꢅ ꢆꢇꢈꢅ 1
NH-CO), 7.76 (d, J = 1.7 Hz, 1H, Ph-H), 7.67 (dd, J = 8.5, 1.7
Hz, 1H, Ph-H), 7.60 (d, J = 8.5 Hz, 1H, Ph-H), 7.51 (s, 1H,
Pyrazole-H), 7.18 (d, J = 2.0 Hz, 1H, Ph-H), 7.14 (d, J = 2.0 Hz,
1H, Ph-H), 6.19 (d, J = 4.8 Hz, 1H, Ph-CO-NH), 2.91 (d, J = 4.8
Hz, 3H, NHCH3), 2.13 (s, 3H, Ph-CH3). 13C NMR (101 MHz,
CDCl3) ꢁ 168.87, 156.64, 144.48, 138.62, 138.59, 138.21,
135.66, 133.22, 130.92, 130.72, 130.46, 130.38, 130.04, 129.70,
127.53, 125.86, 124.38, 122.23, 106.90, 26.80, 18.46. Anal. calcd
for C21H14Cl2F6N4O2: C, 46.77; H, 2.62; N, 10.39; found: C,
46.80; H, 2.76; N, 10.50.
201
H NMR (400 MHz, CDCl3) ꢁ 10.28 (s, 1H, Ph-
4.1.4.7. 1-(5-bromo-2-chlorophenyl)-N-(4-bromo-2-methyl-6-
(methylcarbamoyl)phenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
ꢂꢉꢋꢋꢅꢆꢇꢈꢅ
carboxamide (7g). Yellow solid, yield 63.4%, mp 265
1H NMR (400 MHz, DMSO-d6) ꢁ 10.36 (s, 1H, Ph-NH-CO),
8.33 (d, J = 4.5 Hz, 1H, Ph-CO-NH), 7.97 (d, J = 2.1 Hz, 1H, Ph-
H), 7.77 (dd, J = 8.7, 2.1 Hz, 1H, Ph-H), 7.75 (s, 1H, Pyrazole-
H), 7.63 (d, J = 1.7 Hz, 1H, Ph-H), 7.61 (d, J = 8.7 Hz, 1H, Ph-
H), 7.48 (d, J = 1.7 Hz, 1H, Ph-H), 2.66 (d, J = 4.5 Hz, 3H,
NHCH3), 2.18 (s, 3H, Ph-CH3). 13C NMR (101 MHz, DMSO-d6)
ꢁ 166.52, 155.99, 142.89, 139.78, 139.46, 139.08, 136.70,
134.61, 134.52, 132.37, 132.18, 131.61, 130.41, 128.69, 125.27,
122.64, 120.25, 107.04, 26.57, 18.02. Anal. calcd for
C20H14Br2ClF3N4O2: C, 40.40; H, 2.37; N, 9.42; found: C, 40.46;
H, 2.45; N, 9.53.
4.1.4.12. N-(4-bromo-2-methyl-6-(methylcarbamoyl)phenyl)-
1-(2-chloro-5-(trifluoromethyl)phenyl)-3-(trifluoromethyl)-1H-
pyrazole-5-carboxamide (7l). Yellow solid, yield 62.9%, mp
ꢂꢉꢏꢌꢅꢆꢇꢈ1
NH-CO), 8.33 (s, 1H, Ph-CO-NH), 8.17 (d, J = 1.9 Hz, Ph-H),
7.96 (dd, J = 8.3, 1.9 Hz, 1H), 7.91 (d, J = 8.3 Hz, 1H), 7.78 (s,
1H, Pyrazole-H), 7.63 (s, 1H, Ph-H), 7.48 (s, 1H, Ph-H), 2.65 (s,
1H, NHCH3), 2.17 (s, 1H, Ph-CH3). 13C NMR (101 MHz,
DMSO-d6) ꢁ 168.92, 156.60, 144.52, 138.69, 138.63, 138.31,
135.76, 133.28, 130.70, 129.76, 127.60, 127.54, 127.51, 127.42,
126.00, 124.28, 122.11, 121.76, 106.60, 26.77, 17.77. Anal. calcd
for C21H14BrClF6N4O2: C, 43.21; H, 2.42; N, 9.60; found: C,
43.31; H, 2.56; N, 9.54.
207
H NMR(400 MHz, DMSO-d6) ꢁ 10.39 (s, 1H, Ph-
4.1.4.8. N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-1-
(2-chloro-5-iodophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
ꢂꢉꢄꢎꢅꢆꢇꢈꢅ
carboxamide (7h). Yellow solid, yield 65.1%, mp 278
4.1.4.13. N-(4-chloro-2-methyl-6-(methylcarbamoyl)phenyl)-
1-(2,5-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-
1H NMR (400 MHz, DMSO-d6) ꢁ 10.34 (s, 1H, Ph-NH-CO),
8.32 (d, J = 4.5 Hz, 1H, Ph-CO-NH), 8.01 (d, J = 2.0 Hz, 1H, Ph-
H), 7.89 (dd, J = 8.5, 2.0 Hz, 1H, Ph-H), 7.72 (s, 1H, Pyrazole-
H), 7.49 (d, J = 1.9 Hz, 1H, Ph-H), 7.41 (d, J = 8.5 Hz, 1H, Ph-
H), 7.35 (d, J = 2.2 Hz, 1H, Ph-H), 2.66 (d, J = 4.5 Hz, 3H,
carboxamide (7m). Yellow solid, yield 65.7%, mp 250−251 °C;
1H NMR (400 MHz, DMSO-d6) ꢁ 10.40 (s, 1H, Ph-NH-CO),
8.31 (d, J = 3.9 Hz, 1H, Ph-CO-NH), 7.68 – 7.63 (m, 2H,
Pyrazole-H and Ph-H), 7.50 (s, 1H, Ph-H)7.47 – 7.42 (m, 2H,