White brown colored solid, Yield: 60%; mp: 296-300 °C; 1H NMR (500 MHz, DMSO-d6); δ 3.67 (s, 3H), 3.88 (s, 6H), 7.17 (s, 2H), 7.47 (d,
1H), 7.74 (d, 2H), 8.15 (d, 1H), 8.27 (s, 1H), 8.56 (s, 1H), 11.86 (bs, 1H), 13.53 (bs, 1H), 13.99 (bs, 1H); 13C NMR (125 MHz, CDCl3); δ
56.1, 60.8, 100.7, 102.3, 124.1, 125.6, 126.1, 127.3, 131.0, 136.3, 139.2, 147.6, 148.3, 153.1, 157.6. MS (ESI) m/z 515 [M+H]; HR-MS
(ESI) m/z for C24H22N6O4F3 calculated m/z: 515.10302, found m/z: 515.10556.
(E)-3-(4-(trifluoromethyl)phenyl)-N'-((3-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)methylene)-
1H-pyrazole-5-carbohydrazide (13n)
Yellow colored solid, Yield: 63%; mp: 235-240 °C; 1H NMR (400 MHz, DMSO-d6) δ 7.31 (s, 1H), 7.46 (s, 1H), 7.74 (m, 4H), 8.20 (m, 4H),
8.56 (s, 1H), 11.99 (bs,1H), 14.44 (bs ,1H); 13C NMR (125 MHz, DMSO-d6) δ 101.3, 124.1, 125.6, 126.1, 131.0, 133.6, 136.3, 139.2, 147.3,
147.6, 148.6, 157.6. MS (ESI) m/z 493 [M+H]; HR-MS (ESI) m/z for C22H14N6OF6 calculated m/z: 493.11902, found m/z: 493.12346.
(E)-N'-((3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene)-3-(4-(trifluoromethyl)phenyl)-1H-
pyrazole-5-carbohydrazide (13o)
Yellow colored solid, Yield: 70%; mp: 258-260 °C; 1H NMR (400 MHz, DMSO-d6); δ 6.07 (s, 2H), 7.01 (s, 2H), 7.34 (s, 1H), 7.40 (s, 2H),
7.73 (s, 2H), 7.77 (d, 1H), 8.16 (Bs, 1H), 8.24 (s, 1H), 11.91 (bs, 1H), 11.98 (bs, 1H); 13C NMR (125 MHz, DMSO-d6) δ 101.2, 102.3,
108.4, 108.5, 120.8, 124.1, 125.6, 126.1, 128.3, 131.0, 133.6, 139.2, 147.6, 148.8, 149.3, 157.6. MS (ESI) m/z 469 [M+H]; HR-MS (ESI)
m/z for C22H15N6O3F3 calculated m/z: 469.12305, found m/z: 469.40366
(E)-3-(3,4-dichlorophenyl)-N'-((3-(3,4-dimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-1H-pyrazole-5-
carbohydrazide (13p)
White colored solid, Yield: 65%; mp: 274-277 °C; 1H NMR (400 MHz, DMSO-d6) δ 3.90 (d, 6H), 6.98 (s, 2H), 7.36 (m, 2H), 7.57 (Bs, 1H),
7.74 (d, 1H), 7.98 (m, 2H), 8.54 (s, 1H), 11.80 (bs, 1H), 13.77 (bs, 1H), 13.97 (bs ,1H); 13C NMR (125 MHz, DMSO-d6) δ 55.50, 55.58,
107.7, 108.9, 110.6, 112.0, 117.9, 121.1, 123.4, 124.2, 125.1, 125.8, 127.0, 129.1, 141.2, 143.3, 147.5, 147.3, 149.0, 169.2. MS (ESI) m/z
485 [M+H]; HR-MS (ESI) m/z for C22H19N6O3Cl2 calculated m/z: 485.06902, found m/z: 485.08904
(E)-3-(3,4-dichlorophenyl)-N'-((3-(3,4,5-
trimethoxyphenyl)-1H-pyrazol-5-yl)methylene)-1H-pyrazole-5-carbohydrazide (13q)
Pale yellow colored solid, Yield: 60%; mp: 272-275 °C; 1H NMR (500 MHz, CDCl3) δ 3.83 (s, 3H), 3.88 (s, 6H), 6.98 (s, 1H), 7.02 (s, 1H),
7.23 (s, 2H), 7.46 (d, 1H), 7.56 (d, 1H), 7.91 (s, 1H), 8.45 (s, 1H), 11.86 (bs, 1H), 13.99 (bs, 1H); 13C NMR (125 MHz, CDCl3) 56.0, 60.0
101.1, 101.3, 102.8, 105.7, 105.8, 108.7, 119.0, 119.3, 137.5, 147.1, 147.5, 147.7, 153.4, MS (ESI) m/z 515 [M+H]; HR-MS (ESI) m/z for
C23H21N6O4Cl2 calculated m/z: 515.10325, found m/z: 515.10556
(E)-3-(3,4-dichlorophenyl)-N'-((3-(4-(trifluoromethyl)phenyl)-1H-pyrazol-5-yl)methylene)-1H-
pyrazole-5-carbohydrazide (13r)
Yellow colored solid, Yield: 63%; mp: 255-260 °C; 1H NMR (500 MHz, DMSO-d6) δ 7.02 (s, 2H), 7.46 (d, 2H), 7.49 (d, 1H), 7.59 (d, 1H),
7.76 ( d, 1H), 7.86 (d, 1H), 8.56 (s, 1H), 12.86 (bs, 1H), 13.99 (bs, 1H); 13C NMR (125 MHz, DMSO-d6) 101.5 102.8, 106.2, 107.7, 108.4,
124.3, 125.4, 128.7, 129.0, 138.6, 148.0, 148.8, 163.7. MS (ESI) m/z 493 [M+H]; HR-MS (ESI) m/z for C21H13N6OF3Cl2 calculated m/z:
493.11245, found m/z: 493.12346
(E)-N'-((3-(benzo[d][1,3]dioxol-5-yl)-1H-pyrazol-5-yl)methylene)-3-(3,4-dichlorophenyl)-1H-
pyrazole-5-carbohydrazide (13s)
1
Pale yellow colored solid, Yield: 75%; mp: 240-245 °C; H NMR (500 MHz, DMSO-d6); δ 6.08 (s, 2H), 7.01 (m, 1H), 7.39 (m, 3H), 7.73
(d, 1H), 7.77 (d, 1H), 7.87 (d, 1H), 8.19 (s, 1H), 8.54 (s,1H), 9.91 (s, 1H); 13C NMR (125 MHz, DMSO-d6) δ 101.2, 102.3, 108.4, 108.5,
120.8, 127.0, 128.8, 130.7, 132.5, 132.7, 133.4, 139.2 147.6, 148.8, 149.3, 157.6. MS (ESI) m/z 469 [M+H]; HR-MS (ESI) m/z for
C21H15N6O3Cl2 calculated m/z: 469.05772, found m/z: 469.06031
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