Vol. 66, No. 4 (2018)
Chem. Pharm. Bull.
361
5-Chloro-3-methyl-1-phenyl-N-((4-(trifluoromethoxy)phenyl)- C18H12ClF4N3O4S: C, 45.25; H, 2.53; N, 8.79. Found: C, 45.33;
sulfonyl)-1H-pyrazole-4-carboxamide (3e)
H, 2.55; N, 8.74.
5-Chloro-1-(4-chlorophenyl)-3-methyl-N-(phenyl-
Light yellow solid, yield 79%; mp 117–119°C; 1H-NMR
(600MHz, CDCl3) δ: 8.71 (s, 1H), 8.23 (d, J=8.6Hz, 2H), sulfonyl)-1H-pyrazole-4-carboxamide (3k)
7.54–7.48 (m, 3H), 7.45 (d, J=7.3Hz, 2H), 7.39 (d, J=8.4Hz,
Light yellow solid, yield 75%; mp 168–170°C; 1H-NMR
2H), 2.49 (s, 3H). 13C-NMR (151MHz, DMSO) δ: 163.17, (600MHz, CDCl3) δ: 8.66 (s, 1H), 8.16 (d, J=7.5Hz, 2H), 7.67
153.83, 150.04, 133.13, 129.76, 129.55, 128.39, 129.38, (t, J=7.5Hz, 1H), 7.58 (t, J=7.8Hz, 2H), 7.49 (d, J=8.7Hz,
126.17, 116.87, 116.72, 114.65, 13.71. MS (ESI): 460.8 2H), 7.41 (d, J=8.7Hz, 2H), 2.47 (s, 3H). 13C-NMR (151MHz,
(C18H13ClF3N3O4S, [M+H]+). Anal. Calcd for C18H13ClF3N3O4S: DMSO) δ: 163.17, 150.21, 139.08, 138.82, 135.32, 133.63,
C, 47.02; H, 2.85; N, 9.14. Found: C, 47.11; H, 2.88; N, 9.21.
5-Chloro-1-(4-fluorophenyl)-3-methyl-N-(phenylsulfonyl)-1H- (ESI): 411.2 (C18H12ClF4N3O4S, [M+H]+). Anal. Calcd for
pyrazole-4-carboxamide (3f) C18H12ClF4N3O4S: C, 49.77; H, 3.19; N, 10.24. Found: C, 49.80;
Light yellow solid, yield 80%; mp 158–160°C; H-NMR H, 3.14; N, 10.30.
131.51, 129.79, 129.57, 129.45, 119.87, 116.84, 13.70. MS
1
(600MHz, CDCl3) δ: 8.65 (s, 1H), 8.16 (d, J=8.6Hz, 2H),
5-Chloro-1-(4-chlorophenyl)-N-((4-chlorophenyl)sulfonyl)-3-
7.67 (t, J=7.5Hz, 1H), 7.58 (t, J=7.8Hz, 2H), 7.44 (dd, J=8.9, methyl-1H-pyrazole-4-carboxamide (3l)
4.7Hz, 2H), 7.21 (t, J=8.5Hz, 2H), 2.47 (s, 3H). 13C-NMR
Light yellow solid, yield 76%; mp 174–176°C; 1H-NMR
(151MHz, DMSO) δ: 163.17, 160.47, 150.22, 139.08, 138.82, (600MHz, CDCl3) δ: 8.67 (s, 1H), 8.10 (d, J=8.6Hz, 2H), 7.55
133.63, 132.81, 129.79, 129.57, 116.84, 116.12, 115.63, 13.70. (d, J=8.6Hz, 2H), 7.49 (d, J=8.7Hz, 2H), 7.42 (d, J=8.7Hz,
MS (ESI): 394.8 (C17H13ClFN3O3S, [M+H]+). Anal. Calcd for 2H), 2.47 (s, 3H). 13C-NMR (151MHz, DMSO) δ: 163.17,
C17H13ClFN3O3S: C, 51.85; H, 3.33; N, 10.67. Found: C, 51.90; 150.27, 138.93, 137.56, 135.32, 133.70, 131.54, 129.47, 129.15,
H, 3.38; N, 10.72.
128.76, 119.84, 116.75, 13.70. MS (ESI): 445.7 (C17H12Cl3N3O3S,
5-Chloro-N-((4-chlorophenyl)sulfonyl)-1-(4-fluorophenyl)-3- [M+H]+). Anal. Calcd for C17H12Cl3N3O3S: C, 45.91; H, 2.72;
methyl-1H-pyrazole-4-carboxamide (3g)
N, 9.45. Found: C, 45.97; H, 2.77; N, 9.51.
5-Chloro-1-(4-chlorophenyl)-3-methyl-N-tosyl-1H-
Light yellow solid, yield 81%; mp 157–159°C; 1H-NMR
(600MHz, CDCl3) δ: 8.67 (s, 1H), 8.10 (d, J=8.6Hz, pyrazole-4-carboxamide (3m)
Light yellow solid, yield 72%; mp 155–157°C; H-NMR
1
2H), 7.55 (d, J=8.6Hz, 2H), 7.44 (dd, J=8.9, 4.7Hz, 2H),
7.21 (t, J=8.4Hz, 2H), 2.47 (s, 3H). 13C-NMR (151MHz, (600MHz, CDCl3) δ: 8.62 (s, 1H), 8.04 (d, J=8.1Hz, 2H), 7.49
DMSO) δ: 163.17, 160.45, 150.21, 138.94, 137.52, 133.63, (d, J=8.6Hz, 2H), 7.41 (d, J=8.6Hz, 2H), 7.37 (d, J=8.1Hz,
132.81, 129.17, 128.75, 116.80, 116.18, 115.67, 13.71. MS 2H), 2.47 (s, 3H), 2.45 (s, 3H). 13C-NMR (151MHz, DMSO) δ:
(ESI): 429.2 (C17H12Cl2FN3O3S, [M+H]+). Anal. Calcd for 163.21, 150.22, 137.89, 137.65, 135.37, 133.63, 131.56, 129.45,
C17H12Cl2FN3O3S: C, 47.68; H, 2.82; N, 9.81. Found: C, 47.73; 129.37, 128.36, 119.84, 116.81, 21.34, 13.73. MS (ESI): 425.3
H, 2.89; N, 9.76.
5-Chloro-1-(4-fluorophenyl)-3-methyl-N-tosyl-1H-pyrazole-4- C, 50.95; H, 3.56; N, 9.90. Found: C, 50.92; H, 3.63; N, 9.96.
carboxamide (3h) 5-Chloro-1-(4-chlorophenyl)-N-((4-methoxyphenyl)-
Light yellow solid, yield 69%; mp 160–162°C; H-NMR sulfonyl)-3-methyl-1H-pyrazole-4-carboxamide (3n)
(C18H15Cl2N3O3S, [M+H]+). Anal. Calcd for C18H15Cl2N3O3S:
1
1
(600MHz, CDCl3) δ: 8.62 (s, 1H), 8.04 (d, J=8.3Hz, 2H),
Light yellow solid, yield 85%; mp 167–169°C; H-NMR
7.48–7.41 (m, 2H), 7.37 (d, J=8.1Hz, 2H), 7.20 (t, J=8.5Hz, (600MHz, CDCl3) δ: 8.63 (s, 1H), 8.09 (d, J=9.0Hz, 2H), 7.49
2H), 2.47 (s, 3H), 2.45 (s, 3H). 13C-NMR (151MHz, DMSO) (d, J=8.8Hz, 2H), 7.41 (d, J=8.8Hz, 2H), 7.02 (d, J=9.0Hz,
δ: 163.16, 160.55, 150.24, 137.81, 137.63, 133.63, 132.81, 2H), 3.89 (s, 3H), 2.47 (s, 3H). 13C-NMR (151MHz, DMSO) δ:
129.34, 128.37, 116.81, 116.13, 115.61, 13.72. MS (ESI): 408.8 163.84, 163.24, 150.27, 135.32, 133.66, 133.12, 131.45, 129.45,
(C18H15ClFN3O3S, [M+H]+). Anal. Calcd for C18H15ClFN3O3S: 126.15, 119.84, 116.14, 114.63, 55.84, 13.76. MS (ESI): 441.3
C, 53.01; H, 3.71; N, 10.30. Found: C, 53.09; H, 3.75; N, 10.26. (C18H15Cl2N3O4S, [M+H]+). Anal. Calcd for C18H15Cl2N3O4S:
5-Chloro-1-(4-fluorophenyl)-N-((4-methoxyphenyl)- C, 49.10; H, 3.43; N, 9.54. Found: C, 49.18; H, 3.48; N, 9.59.
sulfonyl)-3-methyl-1H-pyrazole-4-carboxamide (3i)
5 - C h lo r o -1- (4 - c h lo r o p h e nyl) -3 - m e t hyl - N - ((4 -
Light yellow solid, yield 66%; mp 114–116°C; 1H-NMR (trif luoromethoxy)phenyl)sulfonyl)-1H-pyrazole-4-
(600MHz, CDCl3) δ: 8.62 (s, 1H), 8.09 (d, J=8.9Hz, 2H), carboxamide (3o)
1
7.47–7.40 (m, 2H), 7.20 (t, J=8.4Hz, 2H), 7.02 (d, J=8.9Hz,
Light yellow solid, yield 86%; mp 158–160°C; H-NMR
2H), 3.89 (s, 3H), 2.48 (s, 3H). 13C-NMR (151MHz, DMSO) (600MHz, CDCl3) δ: 8.69 (s, 1H), 8.23 (d, J=8.9Hz, 2H), 7.49
δ163.81, 163.21, 160.41, 150.23, 133.63, 133.12, 132.81, 126.12, (d, J=8.7Hz, 2H), 7.40 (dd, J=13.8, 8.7Hz, 4H), 2.48 (s, 3H).
116.84, 116.18, 115.63, 114.63, 55.83, 13.72. MS (ESI): 424.8 13C-NMR (151MHz, DMSO) δ: 163.26, 153.83, 150.27, 135.34,
(C18H15ClFN3O4S, [M+H]+). Anal. Calcd for C18H15ClFN3O4S: 133.71, 133.16, 131.54, 129.74, 129.45, 126.19, 119.87, 116.60,
C, 51.01; H, 3.57; N, 9.91. Found: C, 51.08; H, 3.62; N, 9.97.
5-Chloro-1-(4-fluorophenyl)-3-methyl-N-((4-(trifluoro- Anal. Calcd for C18H12Cl2F3N3O4S: C, 43.74; H, 2.45; N, 8.50.
114.67, 13.70. MS (ESI): 495.2 (C18H12Cl2F3N3O4S, [M+H]+).
methoxy)phenyl)sulfonyl)-1H-pyrazole-4-carboxamide (3j)
Found: C, 43.78; H, 2.47; N, 8.57.
5-Chloro-3-methyl-N-(phenylsulfonyl)-1-(p-tolyl)-1H-
Light yellow solid, yield 63%; mp 133–135°C; 1H-NMR
(600MHz, CDCl3) δ: 8.70 (s, 1H), 8.23 (d, J=8.8Hz, pyrazole-4-carboxamide (3p)
1
2H), 7.48–7.42 (m, 2H), 7.39 (d, J=8.4Hz, 2H), 7.21 (t,
Light yellow solid, yield 88%; mp 184–186°C; H-NMR
J=8.4Hz, 2H), 2.48 (s, 3H). 13C-NMR (151MHz, DMSO) (600MHz, CDCl3) δ: 8.69 (s, 1H), 8.16 (d, J=7.4Hz, 2H), 7.66
δ: 163.20, 160.41, 153.84, 150.20, 133.63, 133.14, 132.81, (t, J=7.5Hz, 1H), 7.58 (t, J=7.8Hz, 2H), 7.34–7.28 (m, 4H),
129.74, 126.15, 116.85, 116.18, 115.67, 114.67, 13.73. MS 2.47 (s, 3H), 2.43 (s, 3H). 13C-NMR (151MHz, DMSO) δ:
(ESI): 478.8 (C18H12ClF4N3O4S, [M+H]+). Anal. Calcd for 163.24, 150.27, 139.08, 138.82, 135.84, 134.26, 133.57, 129.79,