KHALLAF ET AL.
11
(
(
(
m, 1H, pyridine-H), 7.85-7.88 (m, 2H, Ar-H), 7.81-7.84
m, 1H, Ar-H), 7.67-7.72 (m, 1H, pyrazole-H), 7.45-7.48
m, 2H, Ar-H), 7.42 (m, 1H, pyridine-H), 7.37 (m, 1H, Ar-
4.8.21 | 1-(6-bromopyridin-2-yl)-N-
(4-chloro-2-(3-(4-methoxyphenyl)-
1,2,4-oxadiazol-5-yl)-6-methylphenyl)-
5-methyl-1H-pyrazole-4-carboxamide 8c5
H), 2.92 (s, 3H, pyrazole-CH ), 2.36 (s, 3H, Ar-CH ). MS
m/z: calcd. for C H BrCl N O (M + H): 583.09. Found
3
3
25
17
2 6 2
1
(M + H): 583.25.
Yield: 45.9%; white solid; H NMR (400 MHz, DMSO-d )
6
δ 10.11 (s, 1H, O C NH ), 8.23 (m, 1H, pyridine-H),
8.03 (m, 1H, pyridine-H), 7.92-7.95 (m, 2H, Ar-H),
4.8.18 | N-(2-(3-(4-bromophenyl)-
1,2,4-oxadiazol-5-yl)-4-chloro-
6-methylphenyl)-1-(6-bromopyridin-
2-yl)-5-methyl-1H-pyrazole-
4-carboxamide 8c2
7.87-7.90 (m, 1H, Ar-H), 7.72-7.78 (m, 1H, pyridine-H),
7.53-7.54 (m, 1H, pyrazole-H), 7.48-7.51 (m, 1H, Ar-H),
6.95-6.98 (m, 2H, Ar-H), 3.85 (s, 3H, Ar-CH ), 2.99 (s, 3H,
3
pyrazole-CH ), 2.43 (s, 3H, Ar-CH ). MS m/z: calcd. for
3
3
C H BrClN O (M + H): 578.9. Found (M + H): 578.1.
26
20
6 3
1
Yield: 66.8%; white solid; H NMR (400 MHz, CDCl ) δ
3
9
.92 (s, 1H, O C NH ), 8.20 (m, 1H, pyridine-H), 8.04
4.8.22 | 1-(6-bromopyridin-2-yl)-N-
(4-chloro-2-methyl-6-(3-(4-nitrophenyl)-
1,2,4-oxadiazol-5-yl)phenyl)-5-methyl-1H-
pyrazole-4-carboxamide 8c6
(m, 1H, pyridine-H), 7.88-7.91 (m, 2H, Ar-H), 7.84-7.86
(m, 1H, Ar-H), 7.74-7.79 (m, 1H, pyrazole-H), 7.59-7.64
(m, 2H, Ar-H), 7.55 (m, 1H, pyridine-H), 7.50 (m, 1H, Ar-
H), 2.98 (s, 3H, pyrazole-CH ), 2.43 (s, 3H, Ar-CH ). MS
m/z: calcd. for C H Br ClN O (M + H): 627.8. Found
3
3
1
Yield: 59.7%; white solid; H NMR (400 MHz, DMSO-d )
25
17
2
6
2
6
(M + H): 627.9.
δ 9.66 (s, 1H, O C NH ), 8.26 (m, 1H, pyridine-H),
8
8
.23-8.25 (m, 1H, pyridine-H), 8.12-8.14 (m, 2H, Ar-H),
.10 (m, 1H, Ar-H), 8.00 (m, 1H, pyridine-H), 7.83-7.85
4
.8.19 | 1-(6-bromopyridin-2-yl)-N-
(m, 1H, pyrazole-H), 7.69-7.71 (m, 1H, Ar-H), 7.44-7.51
(
4-chloro-2-methyl-6-(3-(4-(trifluoromethyl)
(m, 2H, Ar-H), 2.91 (s, 3H, pyrazole-CH ), 2.37 (s, 3H,
3
phenyl)-1,2,4-oxadiazol-5-yl)phenyl)-
Ar-CH ). MS m/z: calcd. for C H BrClN O (M + H):
3
25 17
7 4
5-methyl-1H-pyrazole-4-carboxamide 8c3
593.9. Found (M + H): 593.2.
1
Yield: 64.1%; white solid; H NMR (400 MHz, CDCl ) δ
3
9
8
7
7
1
.86 (s, 1H, O C NH ), 8.22 (m, 1H, pyridine-H),
.11-8.14 (m, 2H, Ar-H), 8.06 (m, 1H, pyridin-H),
.88-7.91 (m, 1H, pyrazole-H), 7.74-7.77 (m, 2H, Ar-H),
.73 (m, 1H, Ar-H), 7.56 (m, 1H, pyridine-H), 7.53 (m,
4.8.23 | 1-(6-bromopyridin-2-yl)-N-
(4-chloro-2-methyl-6-(3-(3-(trifluoromethyl)
phenyl)-1,2,4-oxadiazol-5-yl)phenyl)-
5-methyl-1H-pyrazole-4-carboxamide 8c7
H, Ar-H), 2.99 (s, 3H, pyrazole-CH ), 2.44 (s, 3H, Ar-
3
1
CH ). MS m/z: calcd. for C H BrClF N O (M + H):
Yield: 68.5%; white solid; H NMR (400 MHz, CDCl ) δ
3
26 17
3
6
2
3
6
16.9. Found (M + H): 616.2.
9.81 (s, 1H, O C NH ), 8.27 (m, 1H, Ar-H), 8.21 (m, 1H,
Ar-H), 8.19 (m, 1H, pyridine-H), 8.07 (m, 1H, Ar-H),
7.89-7.92 (m, 1H, pyridine-H), 7.72-7.78 (m, 2H, Ar-H),
4
.8.20 | 1-(6-bromopyridin-2-yl)-N-
7.60-7.65 (m, 1H, pyrazole-H), 7.56-7.57 (m, 1H, pyridine-
H), 7.48-7.50 (m, 1H, Ar-H), 2.99 (s, 3H, pyrazole-CH3),
2.44 (s, 3H, Ar-CH ). MS m/z: calcd. for C H BrClF N O
(
1
4-chloro-2-methyl-6-(3-(p-tolyl)-
,2,4-oxadiazol-5-yl)phenyl)-5-methyl-1H-
3
26 17
3 6 2
pyrazole-4-carboxamide 8c4
(M + H): 616.9. Found (M + H): 616.3.
1
Yield: 60.2%; white solid; H NMR (400 MHz, CDCl ) δ
3
1
0.11 (s, 1H, O C NH ), 8.23 (s, 1H, pyridine-H), 8.03
4.8.24 | 1-(6-bromopyridin-2-yl)-N-
(
(
(
(
m, 1H, pyridine-H), 7.88-7.90 (m, 3H, Ar-H), 7.73-7.78
m, 1H, pyrazole-H), 7.49-7.54 (m, 2H, Ar-H), 7.29
(4-chloro-2-methyl-6-(3-(2-(trifluoromethyl)
phenyl)-1,2,4-oxadiazol-5-yl)phenyl)-
5-methyl-1H-pyrazole-4-carboxamide 8c8
m, 1H, pyridine-H), 2.99 (s, 3H, pyrazole-CH ), 2.43
3
s, 3H, Ar-CH ), 2.40 (s, 3H, Ar-CH ). MS m/z: calcd.
3
3
1
for C H BrClN O (M + H): 562.9. Found (M
Yield: 50.3%; white solid; H NMR (400 MHz, CDCl ) δ
2
6
20
6
2
3
+
H): 562.2.
9.81 (s, 1H, O C NH ), 8.07 (m, 1H, pyridine-H), 8.01