12
METWALLY ET AL.
Pale brown crystals, yield 76% (0.3 g), m.p. > 300ꢀC,
Pale brown crystals, yield 80% (0.4 g), m.p. > 300ꢀC,
IR (KBr) vmax/cm−1; 3323 (NH2), 3206 (NH), 2215 (2CN),
IR (KBr) vmax/cm−1; 3338 (NH2), 3208 (NH), 2217 (2CN),
1
1
1668 (CO); H NMR (DMSO-d6) δ = 4.90 (s, 2H, CH2),
1675 (CO); H NMR (DMSO-d6) δ = 2.25 (s, 3H, CH3),
7.03 (s, 2H, NH2), 7.04-7.87 (m, 9H, Ar), 7.90 (s, 1H, CH),
10.29 (s, 1H, NH); 13C NMR (DMSO) δ = 50.6, 69.7,
103.9, 114.6, 115.6, 119.3, 120.5, 128.9, 130.7, 131.0, 131.6,
135.6, 138.4, 141.8, 144.6, 154.8, 164.2; Anal. Calcd for
C21H15ClN6O: C, 62.61; H, 3.75; Cl, 8.80; N, 20.86.
Found: C, 62.44; H, 3.57; N, 20.63%.
3.75 (s, 3H, OCH3), 3.83 (s, 6H, 2OCH3), 4.87 (s, 2H, CH2),
6.99 (s, 2H, NH2), 7.11 (d, 2H, J = 8.1 Hz, Ar), 7.27 (s, 2H,
Ar), 7.55 (d, 2H, J = 8.1 Hz, Ar), 7.85 (s, 1H, CH), 10.20 (s,
1H, NH); Anal. Calcd for C25H24N6O4: C, 63.55; H,
5.12; N, 17.79. Found: C, 63.72; H, 5.30; N, 17.57%.
2-(5-Amino-3-(2-(4-chlorophenyl)-1-cyanovinyl)-
2-(5-Amino-4-cyano-3-(2-(2,4-dichlorophenyl)-
4-cyano-1H-pyrazol-1-yl)-N-(p-tolyl)acetamide (15j)
Pale brown crystals, yield 74% (0.3 g), >300ꢀC, IR
(KBr) vmax/cm−1; 3332 (NH2), 3202 (NH), 2217 (2CN),
1-cyanovinyl)-1H-pyrazol-1-yl)-N-phenylacetamide (15e)
Brown crystals, yield 88% (0.4 g), m.p. > 300ꢀC, IR
(KBr) vmax/cm−1; 3331 (NH2), 3203 (NH), 2217 (2CN),
1
1660 (CO); H NMR (DMSO-d6) δ = 2.25 (s, 3H, CH3),
1
1670 (CO); H NMR (DMSO-d6) δ = 4.93 (s, 2H, CH2),
4.89 (s, 2H, CH2), 6.99 (s, 2H, NH2), 7.11-7.63 (m, 8H,
Ar), 8.12 (s, 1H, CH), 10.21 (s, 1H, NH); Anal. Calcd for
C22H17ClN6O: C, 63.39; H, 4.11; Cl, 8.50; N, 20.16.
Found: C, 63.56; H, 4.28; N, 20.39%.
7.05 (s, 2H, NH2), 7.07-8.08 (m, 8H, Ar), 8.11 (s, 1H, CH),
10.26 (s, 1H, NH); 13C NMR (DMSO) δ = 50.8, 66.3, 69.5,
107.7, 114.4, 118.9, 120.6, 123.4, 127.6, 128.1, 129.0, 130.1,
134.6, 136.0, 137.5, 138.4, 144.3, 155.0, 164.2; Anal. Calcd
for C21H14Cl2N6O: C, 57.68; H, 3.23; Cl, 16.21; N, 19.22.
Found: C, 57.51; H, 3.41; N, 19.45%.
2-(5-Amino-4-cyano-3-(2-(2,4-dichlorophenyl)-
1-cyanovinyl)-1H-pyrazol-1-yl)-N-(p-tolyl)acetamide (15k)
Pale brown crystals, yield 72% (0.3 g), m.p. > 300ꢀC,
IR (KBr) vmax/cm−1; 3357 (NH2), 3238 (NH), 2209 (2CN),
2-(5-Amino-4-cyano-3-(1-cyano-2-(furan-2-yl)vinyl)-
1H-pyrazol-1-yl)-N-phenyl-acetamide (15f)
1
1693 (CO); H NMR (DMSO-d6) δ = 2.25 (s, 3H, CH3),
Brown crystals, yield 77% (0.3 g), m.p. = 270-272ꢀC,
IR (KBr) vmax/cm−1; 3334 (NH2), 3200 (NH), 2212 (2CN),
4.87 (s, 2H, CH2), 7.01 (s, 2H, NH2), 7.12 (d, 2H,
J = 8.4 Hz, Ar), 7.42 (d, 2H, J = 8.4 Hz, Ar), 7.51-7.90 (m,
3H, Ar), 8.11 (s, 1H, CH), 10.18 (s, 1H, NH); Anal. Calcd
for C22H16Cl2N6O: C, 58.55; H, 3.57; Cl, 15.71; N, 18.62.
Found: C, 58.72; H, 3.39; N, 18.83%.
1
1668 (CO); H NMR (DMSO-d6) δ = 4.88 (s, 2H, CH2),
6.99 (s, 2H, NH2), 7.07-7.97 (m, 8H, Ar), 8.08 (s, 1H, CH),
10.28 (s, 1H, NH); 13C NMR (DMSO) δ = 50.5, 69.5, 98.9,
114.5, 116.0, 118.4, 119.6, 127.6, 128.2, 129.21, 134.5,
135.8, 136.1, 138.4, 144.3, 154.7, 164.2; Anal. Calcd for
C19H14N6O2: C, 63.68; H, 3.94; N, 23.45. Found: C,
63.68; H, 3.94; N, 23.45%.
2-(5-Amino-4-cyano-3-(1-cyano-2-(furan-2-yl)vinyl)-
1H-pyrazol-1-yl)-N-(p-tolyl)-acetamide (15l)
Brown crystals, yield 72% (0.3 g), m.p. > 300ꢀC, IR
(KBr) vmax/cm−1; 3331 (NH2), 3207 (NH), 2213 (2CN),
1
2-(5-Amino-4-cyano-3-(1-cyano-2-phenylvinyl)-1H-
pyrazol-1-yl)-N-(p-tolyl)-acetamide (15g)
1614 (CO); H NMR (DMSO-d6) δ = 2.24 (s, 3H, CH3),
4.87 (s, 2H, CH2), 6.76 (dd, 1H, J = 1.5, 1.5 Hz, Ar), 7.00
(s, 2H, NH2), 7.11 (d, 2H, J = 8.1 Hz, Ar), 7.25 (d, 1H,
J = 3.3 Hz, Ar), 7.46 (d, 2H, J = 8.4 Hz, Ar), 7.69 (d, 1H,
J = 3.3 Hz, Ar), 8.01 (s, 1H, CH), 10.22 (s, 1H, NH); 13C
NMR (DMSO) δ = 20.1, 50.6, 66.3, 69.4, 98.6, 112.5, 113.4,
115.6, 117.3, 118.8, 120.6, 128.4, 132.5, 135.9, 144.4, 148.7,
154.8, 164.0; Anal. Calcd for C20H16N6O2: C, 64.51; H,
4.33; N, 22.57. Found: C, 64.69; H, 4.50; N, 22.35%.
White crystals, yield 68% (0.2 g), m.p. = 290-292ꢀC, IR
(KBr) vmax/cm−1; 3330 (NH2), 3208 (NH), 2217 (2CN),
1
1687 (CO); H NMR (DMSO-d6) δ = 2.25 (s, 3H, CH3),
4.87 (s, 2H, CH2), 7.01 (s, 2H, NH2), 7.11 (d, 2H,
J = 8.4 Hz, Ar), 7.45 (d, 2H, J = 8.4 Hz, Ar), 7.53-7.89 (m,
5H, Ar), 7.91 (s, 1H, CH), 10.20 (s, 1H, NH); Anal. Calcd
for C22H18N6O: C, 69.10; H, 4.74; N, 21.98. Found: C,
69.28; H, 4. 57; N, 21.75%.
2-(5-Amino-4-cyano-3-(1-cyano-2-phenylvinyl)-1H-
2-(5-Amino-4-cyano-3-(2-(2,5-dimethoxyphenyl)-
1-cyanovinyl)-1H-pyrazol-1-yl)-N-(p-tolyl)acetamide (15h)
Yellow crystals, yield 74% (0.3 g), m.p. = 278-280ꢀC, IR
(KBr) vmax/cm−1; 3324 (NH2), 3204 (NH), 2213 (2CN),
1687 (CO); 1H NMR (DMSO-d6) δ = 2.25 (s, 3H, CH3), 3.76
(s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.87 (s, 2H, CH2), 6.99
(s, 2H, NH2), 7.10-7.61 (m, 7H, Ar), 8.19 (s, 1H, CH), 10.19
(s, 1H, NH); Anal. Calcd for C24H22N6O3: C, 65.15; H,
5.01; N, 18.99. Found: C, 65.32; H, 5.16; N, 18.76%.
2-(5-Amino-4-cyano-3-(1-cyano-2-
pyrazol-1-yl)-N-(4-chloro-phenyl)acetamide (15m)
Pale brown crystals, yield 72% (0.3 g), m.p. > 300ꢀC,
IR (KBr) vmax/cm−1; 3343 (NH2), 3212 (NH), 2219 (2CN),
1
1695 (CO); H NMR (DMSO-d6) δ = 4.90 (s, 2H, CH2),
7.02 (s, 2H, NH2), 7.37 (d, 2H, J = 9 Hz, Ar), 7.53-7.59 (m,
3H, Ar), 7.60 (d, 2H, J = 8.7 Hz, Ar), 7.86-7.89 (m, 2H,
Ar), 7.93 (s, 1H, CH), 10.44 (s, 1H, NH); Anal. Calcd for
C21H15ClN6O: C, 62.61; H, 3.75; Cl, 8.80; N, 20.86.
Found: C, 62.44; H, 3.58; N, 20.63%.
2-(5-Amino-4-cyano-3-(2-(2,5-dimethoxyphenyl)-
1-cyanovinyl)-1H-pyrazol-1-yl)-N-(4-chlorophenyl)acet-
amide (15n)
(3,4,5-trimethoxyphenyl)vinyl)-1H-pyrazol-1-yl)-N-(p-tolyl)
acetamide (15i)