Paper
RSC Advances
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29.15, 128.92, 128.73, 128.43, 128.23, 124.80, 120.50, 119.92,
1-(4-Chlorophenyl)-N-(4-cyano-1-phenyl-1H-pyrazol-5-yl)-
+
08.38, 106.76, 77.2. MS (ESI): 465.1 (C H ClN O, [M + H] ). 3-phenyl-1H-pyrazole-4-carboxamide (5k). Pale yellow crystal,
2
6
18
6
ꢁ
1
Anal. calcd for C H ClN O: C, 67.17; H, 3.69; N, 18.08; found: yield 61%, mp: 230–231 C. H NMR (400 MHz, CDCl ) d 8.90 (s,
2
6
17
6
3
C, 67.25; H, 3.86; N, 18.12%.
1H), 8.09 (d, J ¼ 8.4 Hz, 1H), 7.94–7.89 (m, 2H), 7.85–7.81 (m,
N-(4-Cyano-1-(p-tolyl)-1H-pyrazol-5-yl)-1,3-diphenyl-1H-pyrazole- 2H), 7.60–7.39 (m, 10H). MS (ESI): 465.1 (C H ClN O, [M +
2
6
17
6
ꢁ
+
4
-carboxamide (5d). Pale yellow crystal, yield 63%, mp: 183–185 C. H] ). Anal. calcd for C H ClN O: C, 67.17; H, 3.69; N, 18.08;
26 17 6
1
H NMR (400 MHz, CDCl
3
) d 8.93 (s, 1H), 8.09 (d, J ¼ 8.4 Hz, 1H), found: C, 67.35; H, 3.75; N, 18.12%.
.96–7.91 (m, 2H), 9.90–7.84 (m, 2H), 7.60–7.39 (m, 10H), 2.42 (m,
1-(4-Chlorophenyl)-N-(4-cyano-1-(4-uorophenyl)-1H-pyrazol-
H), C NMR (151 MHz, chloroform-d) d 158.56, 155.73, 143.49, 5-yl)-3-phenyl-1H-pyrazole-4-carboxamide (5l). Pale yellow
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3
1
13
ꢁ
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38.73, 133.34, 130.63, 130.49, 129.81, 129.52, 129.15, 128.93, crystal, yield 61%, mp: 245–247 C. H NMR (400 MHz, CDCl ) d
3
1
28.72, 128.42, 128.23, 124.78, 120.52, 119.92, 108.38, 106.78, 77.2, 8.91 (s, 1H), 8.09 (dt, J ¼ 8.4, 0.9 Hz, 1H), 7.94–7.90 (m, 2H), 7.85–
+
21.15. MS (ESI): 445.2 (C H N O, [M + H] ). Anal. calcd for 7.81 (m, 2H), 7.56–7.43 (m, 9H). MS (ESI): 483.1 (C H ClFN O,
27 21 6
26 16 6
+
C
27 20 6
26 16 6
H N O: C, 72.96; H, 4.54; N, 18.91; found: C, 73.03; H, 4.62; N, [M + H] ). Anal. calcd for C H ClFN O: C, 64.67; H, 3.34; N,
18.98%.
17.40; found: C, 64.83; H, 3.56; N, 17.46%.
N-(4-Cyano-1-(4-nitrophenyl)-1H-pyrazol-5-yl)-1,3-diphenyl-
1-(4-Chlorophenyl)-N-(1-(4-chlorophenyl)-4-cyano-1H-pyrazol-
1
H-pyrazole-4-carboxamide (5e). Pale yellow crystal, yield 67%, 5-yl)-3-phenyl-1H-pyrazole-4-carboxamide (5m). Pale yellow
ꢁ
1
ꢁ
1
mp: 181–183 C. H NMR (400 MHz, CDCl
3
) d 8.92 (s, 1H), 8.08 crystal, yield 63%, mp: 228–230 C. H NMR (400 MHz, CDCl ) d
3
(
7
dd, J ¼ 8.4, 0.8 Hz, 1H), 7.96–7.84 (m, 4H), 7.61–7.50 (m, 4H), 8.90 (s, 1H), 8.09 (dt, J ¼ 8.4, 0.9 Hz, 1H), 7.95–7.88 (m, 2H), 7.85–
+
.50–7.40 (m, 6H). MS (ESI): 476.1 (C H N O , [M + H] ). Anal. 7.80 (m, 2H), 7.57–7.40 (m, 9H). MS (ESI): 499.1 (C H Cl N O,
26 18 7 3
26 16 2 6
+
calcd for C H N O : C, 65.68; H, 3.60; N, 20.62; found: C, [M + H] ). Anal. calcd for C H Cl N O: C, 62.54; H, 3.23; N,
2
6
17
7
3
26 16
2 6
65.84; H, 3.68; N, 20.71%.
16.83; found: C, 62.62; H, 3.41; N, 17.05%.
N-(4-Cyano-1-phenyl-1H-pyrazol-5-yl)-1-(4-uorophenyl)-3-
1-(4-Chlorophenyl)-N-(4-cyano-1-(p-tolyl)-1H-pyrazol-5-yl)-3-
phenyl-1H-pyrazole-4-carboxamide (5f). Pale yellow crystal, yield phenyl-1H-pyrazole-4-carboxamide (5n). Pale yellow crystal,
ꢁ
1
ꢁ
1
6
8
7
1%, mp: 208–210 C. H NMR (400 MHz, CDCl ) d 8.87 (s, 1H), yield 64%, mp: 232–233 C. H NMR (400 MHz, CDCl ) d 8.91 (s,
3
3
.09 (d, J ¼ 8.4 Hz, 1H), 7.96–7.89 (m, 2H), 7.88–7.82 (m, 2H), 1H), 8.09 (d, J ¼ 8.5 Hz, 1H), 7.97–7.88 (m, 2H), 7.86–7.77 (m,
.59–7.38 (m, 7H), 7.31–7.26 (m, 2H), 7.25–7.18 (m, 1H). MS 2H), 7.57–7.52 (m, 2H), 7.46–7.42 (m, 3H), 7.39–7.30 (m, 4H),
+
+
(
ESI): 449.1 (C H FN O, [M + H] ). Anal. calcd for C H FN O: 2.42 (s, 3H). MS (ESI): 479.1 (C H ClN O, [M + H] ). Anal. calcd
26 17 6 26 17 6
27 29 6
C, 69.63; H, 3.82; N, 18.74; found: C, 69.71; H, 3.86; N, 18.83%. for C H ClN O: C, 67.71; H, 4.00; N, 17.55; found: C, 67.91; H,
2
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6
N-(4-Cyano-1-(4-uorophenyl)-1H-pyrazol-5-yl)-1-(4-uorophenyl)- 4.09; N, 17.68%.
-phenyl-1H-pyrazole-4-carboxamide (5g). Pale yellow crystal, yield
1-(4-Chlorophenyl)-N-(4-cyano-1-(4-nitrophenyl)-1H-pyrazol-
) d 10.05 (s, 1H), 5-yl)-3-phenyl-1H-pyrazole-4-carboxamide (5o). Pale yellow
3
ꢁ
1
61%, mp: 162–163 C. H NMR (400 MHz, CDCl
3
ꢁ
1
8
.49 (s, 1H), 7.83–7.75 (m, 5H), 7.57–7.44 (m, 5H), 7.25–7.18 (m, 3H). crystal, yield 65%, mp: 228–230 C. H NMR (400 MHz, CDCl ) d
3
+
MS (ESI): 467.1 (C26
H
16
F
2
N
6
O, [M + H] ). Anal. calcd for 8.91 (s, 1H), 8.09 (d, J ¼ 8.4 Hz, 1H), 7.94–7.89 (m, 2H), 7.85–7.80
C H F N O: C, 66.95; H, 3.46; N, 18.02; found: C, 67.03; H, 3.52; N, (m, 2H), 7.56–7.41 (m, 9H). MS (ESI): 510.1 (C H ClN O , [M +
26
16
2
6
26 16
7 3
+
18.10%.
26 16 7 3
H] ). Anal. calcd for C H ClN O : C, 61.24; H, 3.16; N, 19.23;
N-(1-(4-Chlorophenyl)-4-cyano-1H-pyrazol-5-yl)-1-(4-uo- found: C, 61.44; H, 3.32; N, 19.32%.
rophenyl)-3-phenyl-1H-pyrazole-4-carboxamide (5h). Pale yellow
N-(4-Cyano-1-phenyl-1H-pyrazol-5-yl)-3-phenyl-1-(p-tolyl)-1H-
ꢁ
1
crystal, yield 63%, mp: 167–169 C. H NMR (400 MHz, CDCl
3
) d pyrazole-4-carboxamide (5p). Pale yellow crystal, yield 66%, mp:
ꢁ
0.05 (s, 1H), 8.49 (s, 1H), 7.85–7.75 (m, 4H), 7.54–7.45 (m, 6H), 242–244 C. H NMR (400 MHz, CDCl ) d 10.05 (s, 1H), 8.50 (s,
3
1
1
7
+
.26–7.14 (m, 3H). MS (ESI): 483.1 (C26
16ClFN
C, 64.77; H, 3.42; N, 17.43%.
N-(4-Cyano-1-(p-tolyl)-1H-pyrazol-5-yl)-1-(4-uorophenyl)-3- 73.04; H, 4.61; N, 19.08%.
phenyl-1H-pyrazole-4-carboxamide (5i). Pale yellow crystal, yield
N-(4-Cyano-1-(4-uorophenyl)-1H-pyrazol-5-yl)-3-phenyl-1-(p-
) d 10.05 (s, 1H), tolyl)-1H-pyrazole-4-carboxamide (5q). Pale yellow crystal, yield
H
16ClFN
6
O, [M + H] ). 1H), 7.82 (d, J ¼ 7.7 Hz, 2H), 7.67 (d, J ¼ 8.4 Hz, 2H), 7.58–7.27
+
Anal. calcd for C26
H
6
O: C, 64.67; H, 3.34; N, 17.40; found: (m, 10H), 2.42 (s, 3H). MS (ESI): 445.1 (C H N O, [M + H] ).
2
7
20 6
Anal. calcd for C H N O: C, 72.96; H, 4.54; N, 18.91; found: C,
2
7
20 6
ꢁ
1
6
8
2
5%, mp: 167–169 C. H NMR (400 MHz, CDCl
.49 (s, 1H), 7.82–7.76 (m, 4H), 7.58–7.42 (m, 4H), 7.41–7.27 (m, 63%, mp: 138–140 C. H NMR (400 MHz, CDCl ) d 10.05 (s, 1H),
H), 7.25–7.16 (m, 3H), 2.42 (s, 3H). MS (ESI): 463.2 8.50 (s, 1H), 7.83–7.78 (m, 2H), 7.68–7.66 (m, 2H), 7.54–7.42 (m,
3
ꢁ
1
3
+
(C
27
H
19FN
6
O, [M + H] ). Anal. calcd for C27
H
19FN
6
O: C, 70.12; H, 6H), 7.35–7.26 (m, 3H), 1.58 (s, 3H). MS (ESI): 463.1
+
4.14; N, 18.17; found: C, 70.22; H, 4.33; N, 18.35%.
(C H FN O, [M + H] ). Anal. calcd for C H FN O: C, 70.12; H,
2
7
19
6
27 19
6
N-(4-Cyano-1-(4-nitrophenyl)-1H-pyrazol-5-yl)-1-(4-uorophenyl)- 4.14; N, 18.17; found: C, 70.20; H, 4.26; N, 18.45%.
-phenyl-1H-pyrazole-4-carboxamide (5j). Pale yellow crystal, yield
N-(1-(4-Chlorophenyl)-4-cyano-1H-pyrazol-5-yl)-3-phenyl-
5%, mp: 191–193 C. H NMR (400 MHz, CDCl ) d 10.05 (s, 1H), 1-(p-tolyl)-1H-pyrazole-4-carboxamide (5r). Pale yellow crystal,
3
6
ꢁ
1
3
ꢁ
.49 (s, 1H), 7.82–7.75 (m, 4H), 7.59–7.38 (m, 7H), 7.25–7.16 (m, yield 63%, mp: 172–174 C. H NMR (400 MHz, CDCl ) d 10.04
3
1
8
+
3H). MS (ESI): 494.1 (C26
7 4
H16FN O , [M + H] ). Anal. calcd for (s, 1H), 8.50 (s, 1H), 7.83–7.78 (m, 2H), 7.68–7.66 (m, 2H), 7.54–
16FN : C, 63.28; H, 3.27; N, 19.87; found: C, 63.36; H, 3.35; N, 7.42 (m, 6H), 7.35–7.26 (m, 3H), 2.42 (s, 3H), C NMR (151 MHz,
1
3
26
C H
7 4
O
20.07%.
chloroform-d) d 158.56, 154.64, 149.74, 141.48, 138.02, 136.76,
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RSC Adv., 2015, 5, 55179–55185 | 55183