394
L. Wu, B. Song, P. S. Bhadury, S. Yang, D. Hu, and L. Jin
Vol 48
7.33 (m, 1H, ArH), 7.36 (t, J ¼ 7.15 Hz, 2H, ArH), 7.46 (d, J
¼ 7.45 Hz, 2H, ArH); 13C-NMR (CDCl3, 125 MHz) d: 158.3,
140.2, 139.9, 134.8, 129.9, 128.8, 128.4, 128.0, 123.4, 121.3,
119.2, 112.8, 68.9, 68.5, 51.1, 49.9, 37.3, 23.9, 23.7, 14.5,
10.0, 9.8; 31P-NMR (CDCl3, 200 MHz) d: 21.5; 19F-NMR
(CDCl3, 470 MHz) d: ꢁ61.4; Anal. Calc. for:
C19H24ClF3N3O4P (481.1): C, 47.36; H, 5.02; N, 8.72. Found:
C, 47.53; H, 4.82; N, 8.65.
d: ꢁ61.5; Anal. Calc. for: C19H14ClF3N3O4P (509.15): C, 44.41;
H, 4.71; N, 8.18; Found: C, 45.03; H, 4.53; N, 7.81.
Diethyl((5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-
4-carboxamido)(phenyl)methyl)phosphonate
(J11). Yellow
solid; yield, 68.0%; mp: 152–154ꢀC; IR (KBr): m 3244 (NH),
3068, 3030, 2983, 2931, 2906, 1674 (C¼¼O), 1545, 1490,
1411, 1388, 1315, 1247 (P¼¼O), 1217, 1182, 1024, 1033
(PAOAC), 993, 974, 771, 700 cmꢁ1 1H-NMR (CDCl3, 500
;
Diisopropyl((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyraz-
ole-4-carboxamido)(phenyl)methyl)phosphonate (J8). Yellow
solid; yield, 80%; mp: 130–132ꢀC; IR (KBr): m 3226 (NH),
3061, 3030, 2987, 2934, 1676 (C¼¼O), 1658, 1555, 1506,
1496, 1456, 1379, 1238 (P¼¼O), 1219, 1177, 1140, 1103
MHz) d: 1.12 (t, J ¼ 7.18 Hz, 3H, CCH3), 1.33 (t, J ¼ 7.15
Hz, 3H, CCH3), 3.71–3.79 (m, 1H, OCH2), 3.93–4.00 (m, 1H,
OCH2), 4.09–4.20 (m, 2H, OCH2), 5.63–5.69 (dd, J ¼ 9.15
Hz, J ¼ 20.60 Hz, 1H, NCHP), 7.18–7.21 (br, 1H, NH), 7.31–
7.56 (m, 10H, ArH); 13C-NMR (CDCl3, 125 MHz) d: 158.5,
141.5, 141.2, 136.7, 134.6, 130.1, 129.6, 128.9, 128.5, 128.1,
125.7, 121.3, 119.2, 114.0, 63.8, 63.1, 51.2, 50.0, 16.2, 16.1;
31P-NMR (CDCl3, 200 MHz) d: 21.5; 19F-NMR (CDCl3, 470
MHz) d: ꢁ61.5; Anal. Calc. for: C22H22ClF3N3O4P (515.10):
C, 51.22; H, 4.30; N, 8.15; Found: C, 51.40; H, 3.93; N, 7.86.
Dipropyl((5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-
4-carboxamido)(phenyl)methyl)phosphonate (J12). Yellow solid;
yield, 79%; mp: 142–144ꢀC; IR (KBr): m 3244 (NH), 3067, 3030,
2972, 2940, 2899, 2881, 1681 (C¼¼O), 1455, 1385, 1315, 1238
(P¼¼O), 1215, 1174, 1120, 1139, 1012 (PAOAC), 995, 765, 702,
(PAOAC), 999, 989, 769, 700, 569 cmꢁ1 1H-NMR (CDCl3,
;
500 MHz) d: 0.90 (d, J ¼ 6.30 Hz, 3H, CCH3), 1.24 (d, J ¼
6.30 Hz, 6H, CCH3), 1.31 (d, J ¼ 6.30 Hz, 3H, CCH3), 3.90
(s, 3H, NCH3), 4.43–4.46 (m, 1H, OCH), 4.63–4.69 (m, 1H,
OCH), 5.49–5.55 (dd, J ¼ 9.15 Hz, J ¼ 21.20 Hz, 1H,
NCHP), 7.01–7.03 (br, 1H, NH), 7.29–7.33 (m, 1H, ArH),
7.33 (t, J ¼ 7.15 Hz, 2H, ArH), 7.44 (d, J ¼ 7.45 Hz, 2H,
ArH); 13C-NMR (CDCl3, 125 MHz) d: 158.3, 140.1, 139.9,
135.1, 130.0, 128.6, 128.2, 128.1, 123.4, 121.3, 119.2, 112.9,
72.8, 71.9, 51.9, 50.6, 37.4, 24.3, 24.1, 23.9, 23.1; 31P-NMR
(CDCl3, 200 MHz) d: 19.8; 19F-NMR (CDCl3, 470 MHz) d:
ꢁ61.4; Anal. Calc. for: C19H24ClF3N3O4P (481.1): C, 47.36;
H, 5.02; N, 8.72. Found: C, 47.48; H, 4.48; N, 8.84.
1
569 cmꢁ1; H-NMR (CDCl3, 500 MHz) d: 0.79 (t, J ¼ 7.45 Hz,
3H, CCH3), 0.94 (t, J ¼ 7.45 Hz, 3H, CCH3), 1.45–1.52 (m, 2H,
CCH2C), 1.66–1.71 (m, 2H, CCH2C), 3.58–3.64 (m, 1H, OCH2),
3.83–3.89 (m, 1H, OCH2), 3.99–4.09 (m, 2H, OCH2), 5.64–5.70
(dd, J ¼ 9.15 Hz, J ¼ 20.65 Hz, 1H, NCHP), 7.18–7.20 (br, 1H,
NH), 7.31–7.56 (m, 10H, ArH); 13C-NMR (CDCl3, 125 MHz) d:
158.4, 141.6, 141.3, 136.7, 134.7, 130.2, 129.6, 128.8, 128.4,
128.1, 125.7, 121.3, 119.2, 113.9, 69.2, 68.6, 51.2, 50.0, 23.9,
10.1, 9.9; 31P-NMR (CDCl3, 200 MHz) d: 21.5; 19F-NMR
(CDCl3, 470 MHz) d: ꢁ61.6. Anal. Calc. for: C24H26ClF3N3O4P
(543.13): C, 53.00; H, 4.82; N, 7.73; Found: C, 53.23; H, 4.54;
N, 7.49.
Dibutyl((5-chloro-1-methyl-3-(trifluoromethyl)-1H-pyrazole-
4-arboxamido)(phenyl)methyl)phosphonate (J9). Yellow solid;
yield, 61%; mp: 80–82ꢀC; IR (KBr): m 3209 (NH), 3040, 3032,
2961, 2935, 1670 (C¼¼O), 1560, 1496, 1456, 1385, 1321, 1248
(P¼¼O), 1219, 1177, 1130, 1026, 1005 (PAOAC), 986, 891,
1
708, 700, 563 cmꢁ1; H-NMR (CDCl3, 500 MHz) d: 0.82 (t, J
¼ 7.15 Hz, 3H, CCH3), 0.91 (t, J ¼ 7.15 Hz, 3H, CCH3), 1.18–
1.26 (m, 2H, CCH2C), 1.33–1.45 (m, 4H, CCH2C), 1.60–1.65
(m, 2H, CCH2C) 3.62–3.68 (m, 1H, OCH2), 3.86–3.91 (m, 1H,
OCH2), 3.92 (s, 3H, NCH3), 4.00–4.11 (m, 2H, OCH2), 5.59–
5.65 (dd, J ¼ 9.15 Hz, J ¼ 20.60 Hz, 1H, NCHP), 7.07–7.09
(br, 1H, NH), 7.30–7.32 (m, 1H, ArH), 7.36 (t, J ¼ 7.45 Hz,
2H, ArH), 7.46 (d, J ¼ 7.45 Hz, 2H, ArH); 13C-NMR (CDCl3,
125 MHz) d: 158.3, 140.2, 139.9, 134.8, 129.8, 128.8, 128.3,
128.0, 123.5, 121.3, 119.2, 112.9, 67.3, 66.7, 51.1, 49.9, 37.3,
32.5, 32.3, 18.7, 18.5, 13.6, 13.5; 31P-NMR (CDCl3, 200 MHz)
d: 21.6; 19F-NMR (CDCl3, 470 MHz) d: ꢁ61.4; Anal. Calc. for:
C21H28ClF3N3O4P (509.15): C, 49.47; H, 5.54; N, 8.24. Found:
C, 49.63; H, 5.58; N, 8.08.
Diisopropyl((5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyraz-
ole-4-carboxamido)(phenyl)methyl)phosphonate (J13). Yellow
solid; yield, 73%; mp: 126–128ꢀC; IR (KBr): m 3251 (NH),
3065, 3030, 2980, 2938, 1674 (C¼¼O), 1545, 1489, 1387, 1332,
1315, 1238 (P¼¼O), 1213, 1148, 1099, 1078, 1016 (PAOAC),
1
991, 770, 694, 567 cmꢁ1; H-NMR (CDCl3, 500 MHz) d: 0.92
(d, J ¼ 6.30 Hz, 3H, CCH3), 1.27 (t, J ¼ 6.30 Hz, 6H, CCH3),
1.35 (d, J ¼ 5.70 Hz, 3H, CCH3), 4.44–4.50 (m, 1H, OCH),
4.67–4.73 (m, 1H, OCH), 5.55–5.61 (dd, J ¼ 9.15 Hz, J ¼
20.65 Hz, 1H, NCHP), 7.13–7.16 (br, 1H, NH), 7.30–7.54 (m,
10H, ArH); 13C-NMR (CDCl3, 125 MHz) d: 158.4, 141.6, 141.3,
136.7, 135.1, 130.1, 129.6, 128.8, 128.3, 128.1, 125.8, 121.3,
119.2, 113.9, 72.8, 71.9, 52.0, 50.8, 31.0, 24.4, 21.0, 29.2, 23.1;
31P-NMR (CDCl3, 200 MHz) d: 19.7; 19F-NMR (CDCl3, 470
MHz) d: ꢁ61.5. Anal. Calc. for: C24H26ClF3N3O4P (543.13): C,
53.00; H, 4.82; N, 7.73; Found: C, 53.21; H, 4.72; N, 7.58.
Dibutyl((5-chloro-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-
Bis(2-methoxyethyl)((5-chloro-1-methyl-3-(trifluoromethyl)-
1H-pyrazole-4-carboxamido)(phenyl)methyl)phosphonate
(J10). Yellow solid; yield, 56%; mp: 94–96ꢀC; IR (KBr): m 3238
(NH), 3057, 3032, 2929, 2895, 1666 (C¼¼O), 1551, 1490, 1452,
1317, 1238 (P¼¼O), 1213, 1175, 1132, 1099, 1064, 1041
1
(PAOAC), 979, 962, 727, 698, 579 cmꢁ1; H-NMR (CDCl3, 500
MHz) d: 3.29 (s, 3H, OCH3), 3.33 (s, 3H, OCH3), 3.36–3.41
(m,1H, CH2O), 3.42–3.45 (m, 1H, CH2O), 3.55 (t, J ¼ 4.30 Hz,
2H, CH2O), 3.93 (s, 3H, NCH3), 3.94–3.99 (m, 1H, OCH2),
4.05–4.12 (m, 1H, OCH2), 4.14–4.25 (m, 2H, OCH2), 5.69–5.75
(dd, J ¼ 9.15 Hz, J ¼ 21.20 Hz, 1H, NCHP), 7.26–7.29 (br, 1H,
NH), 7.30–7.33 (m, 1H, ArH), 7.37 (t, J ¼ 7.43 Hz, 2H, ArH),
7.47 (d, J ¼ 7.45 Hz, 2H, ArH); 13C-NMR (CDCl3, 125 MHz) d:
158.5, 140.2, 139.9, 134.6, 129.7, 128.8, 128.3, 128.0, 123.5,
121.3, 119.2, 113.1, 71.4, 66.2, 65.8, 58.8, 51.4, 50.2, 37.3; 31P-
NMR (CDCl3, 200 MHz) d: 22.1; 19F-NMR (CDCl3, 470 MHz)
4-carboxamido)(phenyl)methyl)phosphonate
(J14). Yellow
solid; yield, 78%; mp: 179–181ꢀC; IR (KBr): m 3225 (NH),
3065, 3032, 2961, 2933, 1674 (C¼¼O), 1558, 1497, 1385,
1332, 1315, 1246, 1224 (P¼¼O), 1186, 1153, 1035, 1006
1
(PAOAC), 764, 698, 567 cmꢁ1; H-NMR (CDCl3, 500 MHz)
d: 0.82 (t, J ¼ 7.15 Hz, 3H, CCH3), 0.91 (t, J ¼ 7.45 Hz, 3H,
CCH3), 1.18–1.26 (m, 2H, CCH2C), 1.35–1.46 (m, 4H,
CCH2C), 1.62–1.67 (m, 2H, CCH2C), 3.61–3.67 (m, 1H,
OCH2), 3.87–3.93 (m, 1H, OCH2), 4.02–4.14 (m, 2H, OCH2),
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet