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New Journal of Chemistry
DOI: 10.1039/C6NJ02671K
ARTICLE
Journal Name
2
H), 7.43 (t, J = 7.6 Hz, 4H), 7.37 (t, J = 7.5 Hz, 1H), 7.27 – 7.21 (m, δ 9.03 (s, 1H), 8.75 (s, 1H), 8.17 (d, J = 8.4 Hz, 2H), 7.97 (d, J = 8.5 Hz,
H), 7.18 (d, J = 9.5 Hz, 2H), 6.91 (t, J = 7.8 Hz, 1H), 5.46 (s, 2H), 4.74 2H), 7.69 – 7.64 (m, 2H), 7.47 – 7.42 (m, 4H), 7.37 – 7.29 (m, 1H),
2
1
3
(s, 2H), 3.83 (t, J = 5.7 Hz, 2H), 2.96 (t, J = 5.2 Hz, 2H). C NMR (101 7.27 – 7.20 (m, 2H), 6.96 – 6.92 (m, 1H), 5.51 (s, 2H), 4.72 (s, 2H),
1
3
MHz, DMSO-d
6
) δ 155.28, 145.12, 143.92, 141.36, 138.63, 134.12, 3.83 (t, J = 5.7 Hz, 2H), 2.97 (t, J = 6.7 Hz, 2H). C NMR (101 MHz,
) δ 155.66, 145.62, 144.86, 140.84, 139.75, 139.18, 133.94,
21.77, 119.88, 114.78, 111.48, 52.19, 48.83, 41.67, 24.83. EI-MS 129.14, 128.73, 127.80, 127.60, 127.60, 126.51, 122.91, 122.71,
1
33.39, 129.91, 128.64, 128.24, 127.27, 126.11, 121.88, 121.89, DMSO-d
6
1
+
7
m/z 510.20 (M+H) ; Anal. calcd for C28H24ClN O: (%) C, 65.94; H, 122.38, 121.06, 120.47, 112.02, 44.33, 42.16, 41.14, 22.30. EI-MS
+
4.74; N, 19.23; Found: C, 65.16; H, 4.75; N, 19.89.
m/z 544.19 (M+H) ; Anal. Calcd for C29
24 3 7 3
H F N O : (%) C, 64.08; H,
4
.45; N, 18.04; Found: C, 64.10; H, 4.46; N, 18.05.
1
-((1-(4-bromophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
,7-dihydro-1H-pyrazolo[4,3-c] pyridine-5(4H)-carboxamide (7g) 1-((1-(2-chlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
6
-1
Pale yellow solid (87%); m.p. 150-152 °C; IR (KBr) ʋmax / cm 3492, 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
(7k)
1
-1
3022, 2913, 1657, 1422, 1332, 1055, 680. H NMR (400 MHz, DMSO- Off white solid (88%); m.p. 137-139 °C; IR (KBr) ʋmax / cm 3523,
1
d
6 6
) δ 8.90 (s, 1H), 8.75 (s, 1H), 7.88 (d, J = 8.6 Hz, 2H), 7.78 (d, J = 8.8 3032, 2923, 1675, 1445, , 1052, 602. H NMR (400 MHz, DMSO-d )
Hz, 2H), 7.67 (d, J = 7.6 Hz, 2H), 7.45 (dt, J = 7.8, 3.6 Hz, 4H), 7.33 (t, δ 8.87 (s, 1H), 8.75 (s, 1H), 7.81 (d, J = 9.2 Hz, 2H), 7.69 (d, J = 8.5 Hz,
J = 7.4 Hz, 1H), 7.23 (t, J = 7.8 Hz, 2H), 6.94 (t, J = 7.4 Hz, 1H), 5.48 (s, 2H), 7.40 (t, J = 7.6 Hz, 5H), 7.37 (t, J = 7.5 Hz, 1H), 7.27 – 7.21 (m,
1
3
2
H), 4.71 (s, 2H), 3.82 (t, J = 5.6 Hz, 2H), 2.96 (t, J = 6.0 Hz, 2H).
C
1H), 7.19 (d, J = 9.5 Hz, 2H), 6.99 (t, J = 7.8 Hz, 1H), 5.42 (s, 2H), 4.64
1
3
NMR (101 MHz, DMSO-d
6
) δ 155.66, 145.58, 144.65, 140.84, (s, 2H), 3.84 (t, J = 5.7 Hz, 2H), 2.96 (t, J = 5.2 Hz, 2H). C NMR
) δ 155.28, 145.22, 142.92, 141.36, 138.53,
22.51, 122.43, 122.38, 121.92, 120.42, 112.05, 44.33, 42.24, 41.24, 136.23, 134.12, 133.39, 129.91, 128.64, 128.24, 127.27, 126.11,
1
1
2
39.15, 136.17, 133.95, 133.19, 129.14, 128.74, 127.79, 126.45, (101MHz, DMSO-d
6
+
+2
2.22. EI-MS m/z 554.12(M+H) ; 556.10 (M+H) ; Anal. Calcd for 121.88, 121.89, 121.77, 120.21, 119.88, 114.78, 111.48, 52.19
+
28 7
C H24BrN O: (%) C, 60.66; H, 4.36; N, 17.68; Found: C, 60.68; H, 48.83, 41.67, 24.83. EI-MS m/z 510.15 (M+H) ; EI-MS m/z 510.15
+
4.37; N, 17.69.
(M+H) ; Anal. calcd for C28
7
H24ClN O: (%) C, 65.94; H, 4.74; N, 19.23;
Found: C, 65.16; H, 4.75; N, 19.89.
1
-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
6
(7h) 1-((1-(2-fluorophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
-
1
Light brown solid (80%); m.p.147-149 °C; ; IR (KBr) ʋmax / cm 3485, 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
(7l)
1
-1
30311, 2905, 1658, 1402, 1043, 560. H NMR (400 MHz, DMSO-d
6
)
White solid (91%); m.p. 156-158 °C; IR (KBr) ʋmax / cm 3576, 3031,
1
δ 8.85 (s, 1H), 8.76 (s, 1H), 7.99 (d, J = 9.2 Hz, 2H), 7.76 (d, J = 8.5 Hz, 2925, 1665, 1421, 1330, 1050. H NMR (400 MHz, DMSO-d
6
) δ 8.76
H), 7.46 (t, J = 7.8 Hz, 4H), 7.35 (t, J = 7.5 Hz, 1H), 7.27 – 7.21 (m, (s, 1H), 8.68 (s, 1H), 7.83 (t, J = 7.8 Hz, 1H), 7.68 (d, J = 7.6 Hz, 2H),
H), 7.12 (d, J = 9.3 Hz, 2H), 6.92 (t, J = 7.8 Hz, 1H), 5.47 (s, 2H), 4.69 7.64 – 7.51 (m, 2H), 7.51 – 7.38 (m, 5H), 7.33 (t, J = 7.4 Hz, 1H), 7.24
2
2
1
3
(s, 2H), 3.83 (t, J = 5.8 Hz, 2H), 2.97 (t, J = 5.4 Hz, 2H). C NMR (101 (t, J = 7.7 Hz, 2H), 6.95 (t, J = 7.4 Hz, 1H), 5.51 (s, 2H), 4.72 (s, 2H),
1
3
MHz, DMSO-d
6
) δ 155.48, 145.02, 144.23, 143.72, 140.36, 138.63, 3.83 (t, J = 6.1 Hz, 2H), 2.98 (t, J = 6.3 Hz, 2H). C NMR (101 MHz,
) δ 155.67, 153.06, 145.56, 143.95, 140.85, 139.19, 133.96,
19.98, 116.78, 115.48, 95.15, 45.23, 42.13, 41.67, 23.93. EI-MS 131.82, 129.16, 128.75, 127.80, 126.51, 125.99, 125.74, 125.13,
1
29.91, 128.64, 128.24, 127.27, 126.01, 121.88, 121.86, 121.77, DMSO-d
6
1
+
m/z 602.12 (M+H) ; Anal. Calcd for C28
7
H24IN O: (%) C, 55.92; H, 4.03; 122.38, 120.48, 117.66, 117.47, 112.00, 44.20, 42.16, 41.16, 22.34.
+
N, 16.30; Found: C, 55.94; H, 4.31; N, 16.32.
EI-MS m/z 494.20 (M+H) ; Anal. calcd for C28
7
H24FN O: (%) C, 68.14;
H, 4.90; N, 19.87; Found: C, 68.16; H, 4.91; N, 19.89.
1
-((1-(4-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
6
(7i) 1-((1-(2-bromophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
-1
Light yellow solid (81%); m.p. 144-146 °C; IR (KBr) ʋmax / cm 3505, 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide (7m)
1
-1
3031, 2912, 1675, 1532, 1372, 1027. H NMR (400 MHz, DMSO-d
6
) δ White solid (90%); m.p. 119-121 °C; IR (KBr) ʋmax / cm 3490, 3021,
1
9.08 (s, 1H), 8.74 (s, 1H), 8.48 – 8.40 (m, 2H), 8.28 – 8.19 (m, 2H), 2843, 1650, 1410, 1340, 570. H NMR (400 MHz, DMSO-d
6
) δ 8.75
7.71 – 7.63 (m, 2H), 7.50 – 7.39 (m, 4H), 7.40 – 7.27 (m, 1H), 7.28 – (s, 1H), 8.71 (s, 1H), 7.81(d, J = 9.1 Hz, 2H), 7.67 (d, J = 8.4 Hz, 2H),
7
.18 (m, 2H), 6.94 (tt, J = 7.3, 1.2 Hz, 1H), 5.51 (s, 2H), 4.71 (s, 2H), 7.44 (t, J = 7.9 Hz, 5H), 7.33 (t, J = 7.4 Hz, 1H), 7.26 – 7.20 (m, 1H),
1
3
3.83 (t, J = 5.7 Hz, 2H), 2.97 (t, J = 5.4 Hz, 2H). C NMR (101 MHz, 7.11 (d, J = 9.1 Hz, 2H), 6.94 (t, J = 7.8 Hz, 1H), 5.46 (s, 2H), 4.73 (s,
1
3
DMSO-d
6
) δ 155.65, 147.17, 145.65, 145.10, 141.20, 140.83, 139.19, 2H), 3.82 (t, J = 5.6 Hz, 2H), 2.97 (t, J = 5.4 Hz, 2H). C NMR
) δ 155.21, 145.02, 144.23, 143.72, 140.36,
21.14, 120.47, 112.03, 44.29, 42.15, 41.13, 22.28. EI-MS m/z 139.21, 138.63, 134.24, 133.49, 133.67, 129.91, 128.64, 128.24,
1
1
5
2
33.92, 129.13, 128.74, 127.81, 126.50, 125.96, 122.89, 122.38, (101MHz, DMSO-d
6
+
21.19 (M+H) ; Anal. Calcd for C28
24 8 3
H N O : (%) C, 64.61; H, 4.65; N, 127.27, 126.01, 121.88, 121.86, 121.77, 120.08, 118.12, 48.12,
+
+2
1.53; Found: C, 64.63; H, 4.66; N, 21.55.
44.73, 41.67, 22.83 EI-MS m/z 554.12(M+H) , 556.10 (M+H) ; Anal.
Calcd for C28 O: (%) C, 60.66; H, 4.36; N, 17.68; Found: C,
H24BrN
7
N,3-diphenyl-1-((1-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-
yl)methyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-
carboxamide (7j)
60.68; H, 4.37; N, 17.69.
1-((1-(2-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)-N,3-diphenyl-
-1
White solid (76%); m.p. 246-248 °C; IR (KBr) ʋmax / cm 3505, 3029, 6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
(7n)
1
-1
2
903, 1650, 1402, 1357, 1279, 1045. H NMR (400 MHz, DMSO-d
6
)
White solid (87%); m.p. 188-120 °C; (KBr) ʋmax / cm 3512, 3025,
8
| J. Name., 2012, 00, 1-3
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