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Ph, J = 6.9 Hz); 7.25—7.37 (m, 3 H, CH, Ph); 7.45—7.51 (m, 1 H,
5ꢀCH, py); 7.74 (d, 1 H, 4ꢀCH, py, J = 7.8 Hz); 8.50 (s, 1 H,
2ꢀCH, py); 8.59 (d, 1 H, 6ꢀCH, py, J = 4.7 Hz).
J = 7.8 Hz); 7.51—7.57 (m, 1 H, 5ꢀCH, py); 8.12 (d, 1 H, 4ꢀCH,
py, J = 7.0 Hz); 8.67 (d, 1 H, 6ꢀCH, py, J = 4.1 Hz); 8.93 (s, 1 H,
2ꢀCH, py).
(Z)ꢀN,OꢀDimethylꢀNꢀ(2ꢀphenethyl)nicotinamide oxime (1b)
was isolated by column chromatography on silica gel (eluent:
EtOAc—hexane (3 : 1)). The yield was 28%, oil. Found (%):
C, 71.40; H, 7.02; N, 15.58. C16H19N3O. Calculated (%):
C, 71.35; H, 7.11; N, 15.60. 1H NMR ((CD3)2SO), δ: 2.71 (t, 2 H,
CH2CH2Ph, J = 5.6 Hz); 2.78 (s, 3 H, NMe); 3.08 (t, 2 H,
CH2CH2Ph, J = 5.6 Hz); 3.51 (s, 3 H, OMe); 6.99 (d, 2 H, CH,
Ph, J = 9.0 Hz); 7.16—7.27 (m, 3 H, 2 CH, Ph, 5ꢀCH, py);
7.37—7.48 (m, 2 H, CH, Ph, 4ꢀCH, py); 8.26 (s, 1 H, 2ꢀCH,
py); 8.58 (d, 1 H, 6ꢀCH, py, J = 4.7 Hz).
Nꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylbenzamide
(2d) was isolated by column chromatography on silica gel (eluꢀ
ent: EtOAc). The yield was 31%, m.p. 65—67 °C. Found (%): C,
66.83; H, 5.55; N, 15.52. C15H15N3O2. Calculated (%): C, 66.90;
H, 5.61; N, 15.60. 1H NMR ((CD3)2SO), δ: 3.23 (s, 3 H, NMe);
3.59 (s, 3 H, OMe); 7.30—7.35 (m, 2 H, CH, Ph); 7.37—7.42
(m, 3 H, CH, Ph); 7.43—7.47 (m, 1 H, 5ꢀCH, py); 7.98 (d, 1 H,
4ꢀCH, py, J = 9.3 Hz); 8.57 (d, 1 H, 6ꢀCH, py, J = 5.2 Hz); 8.77
(s, 1 H, 2ꢀCH, py).
Nꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylnaphthꢀ
aleneꢀ1ꢀcarboxamide (2e) was isolated by column chromatoꢀ
graphy on silica gel (eluent: EtOAc). The yield was 33%, m.p.
88—90 °C. Found (%): C, 71.39; H, 5.31; N, 13.20. C19H17N3O2.
Calculated (%): C, 71.46; H, 5.37; N, 13.16. 1H NMR ((CD3)2SO),
δ: 3.28 (s, 3 H, NMe); 3.45 (s, 3 H, OMe); 7.21 (t, 1 H, CH,
naphthyl, J = 7.4 Hz); 7.38—7.45 (m, 2 H, CH, naphthyl);
7.46—7.53 (m, 2 H, naphthyl, J = 9.2 Hz); 7.72 (d, 1 H, CH,
naphthyl, J = 9.4 Hz); 7.75—7.79 (m, 1 H, 5ꢀCH, py); 7.81—7.87
(m, 2 H, CH, naphthyl, 4ꢀCH, py); 8.32 (d, 1 H, 6ꢀCH, py,
J = 6.0 Hz); 8.50 (s, 1 H, 2ꢀCH, py).
Nꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylphenylacetꢀ
amide (2f) was isolated by column chromatography on silica gel
(eluent: EtOAc). The yield was 17%, oil. Found (%): C, 67.78;
H, 5.96; N, 14.89. C16H17N3O2. Calculated (%): C, 67.83;
H, 6.05; N, 14.83. 1H NMR ((CD3)2SO), δ: 2.98 (s, 3 H, NMe);
3.80 (s, 2 H, CH2); 3.92 (s, 3 H, OMe); 7.17—7.22 (m, 2 H, CH,
Ph); 7.23 (m, 3 H, CH, Ph); 7.45—7.49 (m, 1 H, 5ꢀCH, py);
7.87 (d, 1 H, 4ꢀCH, py, J = 7.4 Hz); 8.62 (d, 1 H, 6ꢀCH, py,
J = 3.9 Hz); 8.70 (s, 1 H, 2ꢀCH, py).
Nꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylphenoxyꢀ
acetamide (2g) was isolated by column chromatography on silica
gel (eluent: EtOAc). The yield was 42%, oil. Found (%): C, 64.22;
H, 5.83; N, 13.95. C16H17N3O3. Calculated (%): C, 64.20;
H, 5.72; N, 14.04. 1H NMR ((CD3)2SO), δ: 2.99 (s, 3 H, NMe);
3.80 (s, 3 H, OMe); 4.90 (s, 2 H, CH2); 6.78 (d, 2 H, CH, Ph,
J = 8.9 Hz); 6.93 (t, 1 H, CH, Ph, J = 7.4 Hz); 7.24 (t, 2 H, CH,
Ph, J = 9.2 Hz); 7.51—7.56 (m, 1 H, 5ꢀCH, py); 8.04 (d, 1 H,
4ꢀCH, py, J = 11.0 Hz); 8.66 (d, 1 H, 6ꢀCH, py, J = 5.2 Hz);
8.87 (s, 1 H, 2ꢀCH, py).
(Z)ꢀNꢀ(nꢀButyl)ꢀOꢀmethylnicotinamide oxime (1d) was isoꢀ
lated by column chromatography on silica gel (eluent: EtOAc).
The yield was 68%, oil. Found (%): C, 63.81; H, 8.31; N, 20.33.
C11H17N3O. Calculated (%): C, 63.74; H, 8.27; N, 20.27. 1H NMR
((CD3)2SO), δ: 0.73 (t, 3 H, CH2CH2CH2Me, J = 6.7 Hz);
1.10—1.23 (m, 2 H, CH2CH2CH2Me); 1.25—1.37 (m, 2 H,
CH2CH2CH2Me); 2.86—2.93 (q, 2 H, CH2CH2CH2Me,
J = 6.6 Hz); 3.72 (s, 3 H, OMe); 6.03 (t, 1 H, NH, J = 6.7 Hz);
7.42—7.48 (m, 1 H, 5ꢀCH, py); 7.81 (d, 1 H, 4ꢀCH, py, J = 8.9 Hz);
8.58 (s, 1 H, 2ꢀCH, py); 8.62 (d, 1 H, 6ꢀCH, py, J = 5.6 Hz).
(E)ꢀNꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylcinnamꢀ
amide (2a). A solution of cinnamoyl chloride (0.168 g, 1 mmol)
in CHCl3 (5 mL) was added to a solution of compound 1c (0.138 g,
0.84 mmol) and DMAP (0.122 g, 1 mmol) in CHCl3 (25 mL).
The mixture was refluxed for 6 h, cooled, washed with water
(20 mL), and dried with MgSO4. The solvent was evaporated
in vacuo, the residue was subjected to column chromatography
on silica gel (eluent: EtOAc—hexane (5 : 1)) to obtain comꢀ
pound 7a (0.051 g, 24%), oil. Found (%): C, 69.20; H, 5.76;
N, 14.30. C17H17N3O2. Calculated (%): C, 69.14; H, 5.80; N, 14.23.
1H NMR ((CD3)2SO), δ: 3.14 (s, 3 H, NMe); 3.95 (s, 3 H,
OMe); 6.52 (d, 1 H, PhCH=CH, J = 19.0 Hz); 6.91 (d, 1 H,
PhCH=CH, J = 19.0 Hz); 7.25—7.35 (m, 3 H, CH, Ph); 7.52—7.65
(m, 2 H, CH, Ph); 7.66—7.72 (m, 1 H, 5ꢀCH, py), 8.28 (d, 1 H,
4ꢀCH, py, J = 9.3 Hz); 8.79 (d, 1 H, 6ꢀCH, py, J = 5.0 Hz); 9.04
(s, 1 H, 2ꢀCH, py).
Compounds 2b—g were obtained similarly.
(E)ꢀNꢀButylꢀNꢀ[(Z)ꢀmethoxyiminoꢀ3ꢀpyridylmethyl]cinnamꢀ
amide (2b) was isolated by column chromatography on silica gel
(eluent: EtOAc—hexane (1 : 1)). The yield was 18%, m.p.
43—45 °C. Found (%): C, 71.23; H, 6.91; N, 12.51. C20H23N3O2.
Calculated (%): C, 71.19; H, 6.87; N, 12.45. 1H NMR ((CD3)2SO),
δ: 0,89 (t, 3 H, CH2CH2CH2Me, J = 8.2 Hz); 1.17—1.30 (m, 2 H,
CH2CH2CH2Me); 1.34—1.49 (m, 2 H, CH2CH2CH2Me); 3.43
(t, 2 H, CH2CH2CH2Me, J = 8.5 Hz); 3.85 (s, 3 H, OMe); 6.51
(d, 1 H, PhCH=CH, J = 18.0 Hz); 6.85 (d, 1 H, PhCH=CH,
J = 18.0 Hz); 7.35—7.42 (m, 3 H, CH, Ph); 7.50—7.62 (m, 2 H,
CH, Ph); 7.65—7.71 (m, 1 H, 5ꢀCH, py); 8.06 (d, 1 H, 4ꢀCH,
py, J = 9.0 Hz); 8.67 (d, 1 H, 6ꢀCH, py, J = 4.9 Hz); 8.86 (s, 1 H,
2ꢀCH, py).
(E)ꢀNꢀ[(Z)ꢀMethoxyiminoꢀ3ꢀpyridylmethyl]ꢀNꢀmethylꢀ3ꢀ(4ꢀ
chlorophenyl)propenamide (2c) was isolated by column chromaꢀ
tography on silica gel (eluent: EtOAc—hexane (5 : 1)). The yield
was 25%, m.p. 79—81 °C. Found (%): C, 62.00; H, 4.83;
N, 10.78. C17H16ClN3O2. Calculated (%): C, 61.92; H, 4.89;
N, 10.75. 1H NMR ((CD3)2SO), δ: 3.06 (s, 3 H, NMe); 3.80 (s, 3 H,
OMe); 6.55 (d, 1 H, PhCH=CH, J = 20.0 Hz); 6.91 (d, 1 H,
PhCH=CH, J = 20.0 Hz); 7.50—7.68 (A2В2ꢀsystem, 4 H, C6H4,
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