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1567, 1493, 1446, 1404, 1275, 1092, 1013, 920, 829, 692, 592; H NMR (500 MHz, DMSO) δ:
13.89 (s, 1H), 7.87 – 7.83 (m, 2H), 7.77 (d, J = 8.9 Hz, 4H), 7.52 (d, J = 8.8 Hz, 4H), 7.49 – 7.45
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(m, 3H), 6.80 (d, J = 0.9 Hz, 1H), 5.25 (s, 1H), 2.35 (s, 6H); C NMR (126 MHz, DMSO) δ:
173.33, 165.13, 162.23, 148.72, 147.03, 134.14, 131.78, 130.48, 129.42, 129.33, 129.15, 127.03,
122.43, 100.80, 27.96, 14.52; HRMS (EI): calcd for C30H24Cl2N5O3 [M+H]+ 572.1256,
[M+H+2]+ 574.1256, found 572.1286, 574.1256.
4.5.2.
2-(4-chlorophenyl)-4-((1-(4-chlorophenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)(3-(2-
methoxyphenyl)isoxazol-5-yl)methyl)-5-methyl-1H-pyrazol-3(2H)-one (5b). Yield: 90%, mp
209–211 C. IR (KBr) (ν/cm–1) 3626, 3343, 3137, 3096, 3013, 2974, 2940, 2835, 2790, 2758,
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1742, 1701, 1605, 1573, 1497, 1468, 1402, 1275, 1174, 1088, 1022, 829, 773, 602; 1H NMR (500
MHz, DMSO) δ: 13.96 (s, 1H), 7.78 – 7.74 (m, 4H), 7.70 (dd, J = 7.7, 1.7 Hz, 1H), 7.52 (d, J =
8.8 Hz, 4H), 7.48 – 7.43 (m, 1H), 7.16 (d, J = 8.4 Hz, 1H), 7.03 (t, J = 7.5 Hz, 1H), 6.61 (d, J =
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0.9 Hz, 1H), 5.26 (d, J = 6.1 Hz, 1H), 3.80 (s, 3H), 3.18 (s, 2H), 2.36 (s, 6H); C NMR (126
MHz, DMSO) δ: 171.98, 159.89, 157.30, 154.49, 147.07, 137.76, 135.52, 131.86, 129.36, 129.32,
122.37, 121.14, 117.84, 112.70, 103.53, 56.18, 49.03, 27.85, 11.93; HRMS (EI): calcd for
C31H26Cl2N5O4 [M+H]+ 602.1362, [M+H+2]+ 604.1362, found 602.1394, 604.1369.
4.5.3.
2-(4-chlorophenyl)-4-((1-(4-chlorophenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)(3-(4-
methoxyphenyl)isoxazol-5-yl)methyl)-5-methyl-1H-pyrazol-3(2H)-one (5c). Yield: 87%, mp
151–153 C. IR (KBr) (ν/cm–1) 3647, 3346, 3076, 3001, 2930, 2831, 1723, 1701, 1609, 1573,
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1493, 1429, 1254, 1173, 1092, 1013, 829, 611; H NMR (500 MHz, DMSO) δ: 13.88 (s, 1H),
7.78 (dd, J = 8.6, 6.5 Hz, 6H), 7.52 (d, J = 8.8 Hz, 4H), 7.01 (d, J = 8.8 Hz, 2H), 6.71 (s, 1H),
5.22 (s, 1H), 3.80 (s, 3H), 2.34 (s, 6H); 13C NMR (126 MHz, DMSO) δ: 172.95, 161.83, 161.04,
160.95, 156.20, 147.02, 130.13, 129.32, 128.51, 122.42, 121.56, 114.81, 100.49, 55.69, 27.92,
11.92; HRMS (EI): calcd for C31H26Cl2N5O4 [M+H]+ 602.1362, [M+H+2]+ 604.1362, found
602.1391, 604.1365.
4.5.4.
2-(4-chlorophenyl)-4-((1-(4-chlorophenyl)-5-hydroxy-3-methyl-1H-pyrazol-4-yl)(3-(p-
tolyl)isoxazol-5-yl)methyl)-5-methyl-1H-pyrazol-3(2H)-one (5d). Yield: 87%, mp 219–221 oC. IR
(KBr) (ν/cm–1) 3669, 3360, 3069, 3039, 2954, 2920, 2810, 1738, 1701, 1593, 1579, 1493, 1431,
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1180, 1094, 1012, 826, 654; H NMR (500 MHz, DMSO) δ: 13.89 (s, 1H), 7.77 (d, J = 8.9 Hz,
4H), 7.73 (d, J = 8.1 Hz, 2H), 7.52 (d, J = 8.8 Hz, 4H), 7.27 (d, J = 8.1 Hz, 2H), 6.74 (s, 1H),
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