3JCF = 8.3 Hz), 127.8, 118.1,116.6, 116.3, 112.8, 112.7, 110.4, 63.1 (C-5 pyrazoline), 56.1 (-
OCH3), 56.0 (-OCH3), 43.8 (C-4 pyrazoline). HRMS (ESI-MS) C23H23N3O4SF, Calculated
[M+H]+: 456.1393; Found [M+H]+: 456.1390
4-(3-(4-Chlorophenyl)-5-(2,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
benzenesulfonamide, Compund 13
Cream colour solid, mp 217 °C (208 °C lit), yield 57 %. 1H NMR (DMSO-d6, ppm, 400 MHz)
δ 7.74 (d, J = 8.8 Hz, 2H, Ar-H), 7.56 (d, J = 9.0 Hz, 2H, Ar-H), 7.45 (d, J = 8.8 Hz, 2H, Ar-
H),7.02 (s, 2H, -SO2NH2), 6.98 (d, J = 9.0 Hz, 2H, Ar-H), 6.74 (d, J = 8.4 Hz, 1H, Ar-H),
6.59 (d, J = 2.1 Hz, 1H, Ar-H), 6.34 (dd, J = 8.8, 2.6 Hz, 1H, Ar-H), 5.61 (dd, J = 12.0, 5.1
Hz, 1H, H-5 (pyrazoline)), 3.83 (s, 3H, -OCH3), 3.67 (s, 3H, -OCH3), 3.01 (dd, J = 17.6, 5.1
Hz, 1H, H-4 (pyrazoline)). 13C NMR (DMSO-d6, ppm, 100 MHz) δ 160.8, 157.9, 149.8,
146.3, 134.3, 133.5, 131.5, 129.4, 128.3, 127.8, 127.5, 120.9, 112.5, 105.7, 99.6, 57.9 (C-5
pyrazoline), 56.4 (-OCH3), 55.8 (-OCH3), 42.3 (C-4 pyrazoline). HRMS (ESI-MS)
C23H23N3O4SCl, Calculated [M+H]+: 472.1098; Found [M+H]+: 472.1096
4-(3-(4-Chlorophenyl)-5-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
benzenesulfonamide, Compound 14
Cream colour solid, mp 182 °C (184 °C lit), yield 68 %. 1H NMR (DMSO-d6, ppm, 400 MHz)
δ 7.76 (d, J = 8.8 Hz, 2H, Ar-H), 7.56 (d, J = 9.1 Hz, 2H, Ar-H), 7.47 (d, J = 8.8 Hz, 2H, Ar-
H), 7.07 (d, J = 9.1 Hz, 2H, Ar-H), 7.03 (s, 2H, -SO2NH2), 6.90 (d, J = 2.1 Hz, 1H, Ar-H),
6.84 (d, J = 8.2 Hz, 1H, Ar-H), 6.64 (dd, J = 8.2, 2.1 Hz, 1H, Ar-H),5.51 (dd, J = 12.0, 5.3
Hz, 1H, H-5 (pyrazoline)), 3.88 (dd, J = 17.8, 12.0 Hz, 1H, H-4 (pyrazoline), 3.68 (s, 3H, -
OCH3), 3.65 (s, 3H, -OCH3), 3.14 (dd, J = 17.8, 5.3 Hz, 1H, H-4 (pyrazoline)). 13C NMR
(DMSO-d6, ppm, 100 MHz) δ 149.7, 149.4, 148.8, 146.6, 134.4, 134.3, 133.8, 131.4, 129.5,
128.4, 127.8, 118.1, 112.9, 112.7, 110.3, 63.2, (C-5 pyrazoline), 56.1 (-OCH3), 56.0 (-OCH3),
43.5 (C-4 pyrazoline). HRMS (ESI-MS) C23H23N3O4SCl, Calculated [M+H]+: 472.1098;
Found [M+H]+: 472.1108
4-(3-(4-Bromophenyl)-5-(2,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)
benzenesulfonamide, Compound 15
Cream colour solid, mp 225 °C, yield 55 %. 1H NMR (DMSO-d6, ppm, 400 MHz) δ 7.69 (d, J
= 8.4 Hz, 2H, Ar-H), 7.61 (d, J = 8.4 Hz, 2H, Ar-H), 7.57 (d, J =8.8 Hz, 2H, Ar-H), 7.01 (d, J
= 6.2 Hz, 2H, Ar-H), 6.98 (s, 2H, -SO2NH2), 6.75 (d, J = 8.4 Hz, 1H, Ar-H), 6.62 (d, J = 2.3
Hz, 1H, Ar-H), 6.39 (dd, J = 8.3, 2.3 Hz, 1H, Ar-H), 5.64 (dd, J = 12.1, 5.0 Hz, 1H, H-5
(pyrazoline)), 3.85 (s, 3H, -OCH3), 3.69 (s, 3H, -OCH3), 3.04 (dd, J = 17.6, 5.0 Hz, 1H, H-4
(pyrazoline)). 13C NMR (DMSO-d6, ppm, 100 MHz) δ 160.8, 157.8, 149.8, 146.3, 133.7,
13