Molecules 2020, 25, 3500
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138.69, 137.84, 133.65, 131.28, 131.10, 129.52, 129.27, 128.88, 127.32, 124.77, 124.13, 119.78; HRMS calcd.
for C20H11Cl3N4O2 [M + Na]+ 466.9840, found 466.9840.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(o-tolyl)benzamide 7b. Yellow solid,
yield 77%, m.p. 220–223 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ
10.60 (s, 1H), 8.34 (d, J = 9.0 Hz, 1H),
8.21 (d, J = 7.0 Hz, 2H), 7.91 (d, J = 9.0 Hz, 1H), 7.83 (d, J = 9.0 Hz, 1H), 7.61 (d, J = 8.5Hz, 2H), 7.17 (d,
J = 8.5 Hz, 2H), 2.29 (s, 3H); 13C-NMR (500 MHz, DMSO-d6)
171.72, 167.26, 163.68, 148.59, 143.31,
δ
139.68, 137.90, 136.19, 133.65, 133.12, 131.25, 131.07, 129.43, 129.24, 129.21, 127.31, 124.73, 119.76, 20.52;
HRMS calcd. for C21H13Cl3N4O2 [M + Na]+ 480.9996, found 480.9995.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(m-tolyl)benzamide 7c. Yellow solid,
yield 74%, m.p. 260–261 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ
10.69 (s, 1H), 8.35 (d, J = 8.5 Hz, 1H),
8.25–8.17 (m, 2H), 7.92 (d, J = 9.0 Hz, 1H), 7.83 (d, J = 9.0 Hz, 1H), 7.60 (s, 1H), 7.51 (d, J = 8.5 Hz, 1H),
7.25 (t, J = 8.0 Hz, 1H), 6.96 (d, J = 7.5 Hz, 1H), 2.32 (s, 3H); 13C-NMR (500 MHz, DMSO-d6)
171.73,
δ
167.27, 163.88, 148.60, 143.34, 139.70, 138.63, 138.10, 137.90, 133.65, 131.27, 131.08, 129.47, 129.27, 128.69,
127.30, 124.80, 124.74, 120.29, 117.01, 21.22; HRMS calcd. for C21H13Cl3N4O2 [M + Na]+ 480.9996,
found 480.9998.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(p-tolyl)benzamide 7d. White solid,
yield 68%, m.p. 230–232 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ 10.19 (s, 1H), 8.36 (d, J =10 Hz, 1H), 8.27
(d, J = 1.9 Hz, 1H), 8.24–8.18 (m, 1H), 7.93 (d, J = 8.5 Hz, 1H), 7.84 (d, J = 8.4 Hz, 1H), 7.50 (d, J = 7.7 Hz,
1H), 7.29 (d, J = 7.3 Hz, 1H), 7.25 (t, J = 7.3 Hz, 2H), 7.20–7.16 (m, 1H), 2.32 (s, 3H); 13C-NMR (500 MHz,
DMSO-d6) δ 171.76, 167.31, 164.23, 148.63, 143.34, 139.74, 137.98, 135.55, 133.66, 132.97, 131.28, 131.08,
129.43, 129.28, 127.40, 126.19, 126.12, 126.04, 124.74, 18.01; HRMS calcd. for C21H13Cl3N4O2 [M + Na]+
480.9996, found 480.9995.
N-(4-(tert-butyl)phenyl)-2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)benzamide 7e. Grey
solid, yield 69%, m.p. 208–210 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ
10.64 (s, 1H), 8.35 (d, J = 9.0 Hz,1H),
8.23–8.18 (m, 2H), 7.92 (d, J = 8.5 Hz, 1H), 7.83 (d, J = 9.0 Hz, 1H), 7.64 (d, J = 8.5 Hz, 2H), 7.38 (d,
J = 8.5 Hz, 2H), 1.28 (s, 3H); 13C-NMR (500 MHz, DMSO-d6)
171.70, 167.25, 163.71, 148.58, 146.49,
δ
143.31, 139.67, 137.91, 136.12, 133.65, 131.24, 131.05, 129.41, 129.24, 127.28, 126.44, 125.44, 124.71, 119.54,
34.09, 31.18; HRMS calcd. for C24H19Cl3N4O2 [M + Na]+ 523.0466, found 523.0466.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(3-(trifluoromethyl)phenyl)benzamide 7f
White solid, yield 77%, m.p. 191–195 ◦C, H-NMR (500 MHz, DMSO-d6)
11.02 (s, 1H), 8.30 (d, J = 8.5
Hz, 1H), 8.25 (s, 1H), 8.19 (s, 2H), 7.87 (d, J = 8.5 Hz, 2H), 7.81 (d, J = 8.5 Hz, 1H), 7.58 (t, 1H), 7.45 (d,
J = 7.5 Hz, 1H); 13C-NMR (500 MHz, DMSO-d6)
171.76, 167.24, 164.35, 148.61, 143.32, 139.67, 139.42,
.
δ
δ
137.30, 133.66, 131.27, 131.15, 130.19, 129.81, 129.26, 127.45, 124.84, 123.37, 120.48, 115.84; HRMS calcd.
for C21H10Cl3F3N4O2 [M + Na]+ 534.9714, found 534.9717.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(2,4-dimethylphenyl)benzamide 7g
.
Yellow solid, yield 60%, m.p. 225–226 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ
10.09 (s, 1H), 8.37 (d, J = 8.5
Hz, 1H), 8.25 (d, J = 2.0 Hz, 1H), 8.22 (d, J = 2.0 Hz,1H), 8.20 (d, J = 2.0 Hz, 1H), 7.94 (d, J = 8.5 Hz, 1H),
7.84 (d, J = 8.0 Hz, 1H), 7.35 (d, J = 8.0 Hz, 1H), 7.09 (s, 1H), 7.04 (d, J = 8.0 Hz, 1H), 2.29 (s, 3H), 2.27 (s,
3H); 13C-NMR (500 MHz, DMSO-d6)
δ 171.76, 167.31, 164.23, 148.62, 143.34, 139.75, 138.05, 135.33,
133.65, 132.94, 132.83, 131.27, 131.07, 130.98, 129.37, 129.28, 127.38, 126.61, 125.99, 124.71, 20.56, 17.92;
HRMS calcd. for C22H15Cl3N4O2 [M + Na]+ 495.0153, found 495.0154.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(2-fluorophenyl)benzamide 7h. Yellow
solid, yield 60%, m.p. 203–207 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ
10.57 (s, 1H), 8.35 (d, J = 8.5 Hz,
1H), 8.27–8.19 (m, 2H), 7.92 (d, J = 8.5 Hz, 1H), 7.90–7.86 (m, 1H), 7.83 (d, J = 8.0 Hz, 1H), 7.35–7.21
(m, 3H); 13C-NMR (500 MHz, DMSO-d6)
171.78, 167.30, 164.41, 148.65, 143.34, 139.73, 137.35, 133.79,
δ
131.29, 131.10, 129.65, 129.29, 127.54, 126.81 (d, J = 7.5 Hz), 125.70, 125.28, 125.19, 124.69, 124.51 (d,
J = 3.0 Hz), 115.88 (d, J = 19.0 Hz); HRMS calcd. for C20H10Cl3FN4O2 [M + Na]+ 484.9746, found
484.9747.
2-chloro-5-(5-(3,6-dichloropyridin-2-yl)-1,2,4-oxadiazol-3-yl)-N-(3-fluorophenyl)benzamide 7i. Yellow
solid, yield 62%, m.p. 228–230 ◦C, 1H-NMR (500 MHz, DMSO-d6)
δ 10.91 (s, 1H), 8.35 (d, J = 9.0 Hz,