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New Journal of Chemistry
Page 8 of 12
DOI: 10.1039/C5NJ02566D
ARTICLE
Journal Name
(m, 3H), 7.72 (dd, 2H, J = 1.6 Hz, J = 4.8 Hz), 7.77 (s, 1H), 7.84 127.6, 129.2, 130.0, 133.1, 135.2, 137.9, 142.5, 147.3, 148.1,
(d, 1H, J = 8.4 Hz), 8.40 (s, 1H), 8.74 (d, 2H, J = 6.0 Hz); 13C NMR 159.7, 163.1; ESI-MS (m/z): Calcd. 443.89, found 443.50 (M+);
(100 MHz, DMSO-d6): 21.9 (Ar-CH3), 52.5 (N-CH2), 123.5, 125.9, Anal. Calcd. (%) for C24H18ClN5O2: C, 64.94; H, 4.09; N, 15.78.
126.2, 126.8, 127.3, 128.4, 129.1, 132.3, 134.0, 137.5, 139.2, Found: C, 64.79; H, 4.22; N, 15.87.
140.8, 145.5, 148.2, 153.6, 158.5, 162.4; ESI-MS (m/z): Calcd. 6.1.2.9.
N-((2-chloro-6-methoxyquinolin-3-yl)methyl)-N,5-
427.89, found 427.45 (M+); Anal. Calcd. (%) for C24H18ClN5O: C, diphenyl-1,3,4-oxadiazol-2-amine (8i
)
67.37; H, 4.24; N, 16.37. Found: C, 67.42; H, 4.19; N, 16.22.
Yield 78%; white solid; m.p. 237°C; IR (νmax, cm-1): 1606 (C=N
1
6.1.2.5. N-((2-chloro-6-methylquinolin-3-yl)methyl)-N-phenyl-5- str.), 1237 (C-O-C str.), 1066(N-N str.), 758 (C-Cl str.); H NMR
(pyridin-3-yl)-1,3,4-oxadiazol-2-amine (8e
)
(400 MHz, DMSO-d6): 3.84 (s, 3H, Ar-OCH3), 5.39 (s, 2H, N-CH2),
Yield 78%; yellow solid; m.p. 231°C; IR (νmax, cm-1): 1612 (C=N 7.26 (t, 1H, J = 7.2 Hz), 7.40-7.54 (m, 7H), 7.67 (d, 2H, J = 8.0
str.), 1239 (C-O-C str.), 1059 (N-N str.), 756 (C-Cl str.); H NMR Hz), 7.79-7.86 (m, 3H), 8.38 (s, 1H); 13C NMR (100 MHz, DMSO-
1
(400 MHz, DMSO-d6): 2.44 (s, 3H, Ar-CH3), 5.42 (s, 2H, N-CH2), d6): 52.8 (N-CH2), 56.0 (Ar-OCH3), 88.4, 106.3, 123.5, 124.2,
7.37 (t, 1H, J = 7.2 Hz), 7.43 (t, 2H, J = 8.0 Hz), 7.45-7.68 (m, 125.0, 125.8, 126.4, 127.2, 128.7, 129.7, 131.4, 136.4, 137.5,
4H), 7.75 (s, 1H), 7.83 (d, 1H, J = 8.4 Hz), 8.15 (d, 1H, J = 8.0 141.6, 146.2, 148.8, 158.3, 162.5; ESI-MS (m/z): Calcd. 442.90,
Hz), 8.38 (s, 1H), 8.70 (d, 1H, J = 4.8 Hz), 8.98 (d, 1H, J = 1.6 Hz); found 442.50 (M+); Anal. Calcd. (%) for C25H19ClN4O2: C, 67.80;
13C NMR (100 MHz, DMSO-d6): 22.1 (Ar-CH3), 52.8 (N-CH2), H, 4.32; N, 12.65. Found: C, 67.93; H, 4.41; N, 12.78.
122.8, 125.4, 125.8, 126.4, 128.2, 128.6, 129.4, 130.0, 131.1, 6.1.2.10.
N-((2,6-dichloroquinolin-3-yl)methyl)-N-phenyl-5-
132.8, 133.9, 138.5, 140.4, 142.5, 144.1, 147.3, 158.1, 161.8; (pyridin-4-yl)-1,3,4-oxadiazol-2-amine (8j
)
ESI-MS (m/z): Calcd. 427.89, found 428.10 (M+); Anal. Calcd. Yield 73%; brown solid; m.p. 233°C; IR (νmax, cm-1): 1616 (C=N
1
(%) for C24H18ClN5O: C, 67.37; H, 4.24; N, 16.37. Found: C, str.), 1234 (C-O-C str.), 1033(N-N str.), 762 (C-Cl str.); H NMR
67.29; H, 4.33; N, 16.45.
6.1.2.6. N-((2-chloro-6-methylquinolin-3-yl)methyl)-N,5- Hz), 7.46 (t, 2H, J = 8.0 Hz), 7.68-7.73 (m, 4H), 7.81 (dd, 1H, J =
diphenyl-1,3,4-oxadiazol-2-amine (8f
(400 MHz, DMSO-d6): 5.43 (s, 2H, N-CH2), 7.29 (t, 1H, J = 7.2
)
2.4 Hz, J = 9.2 Hz), 7.98 (d, 1H, J = 8.8 Hz), 8.17 (d, 1H, J = 2.4
Yield 74%; white solid; m.p. 239°C; IR (νmax, cm-1): 1611 (C=N Hz), 8.51 (s, 1H), 8.74 (dd, 2H, J = 1.6 Hz, J = 4.8 Hz); 13C NMR
1
str.), 1242 (C-O-C str.), 1054 (N-N str.), 764 (C-Cl str.); H NMR (100 MHz, DMSO-d6): 53.1 (N-CH2), 119.9, 124.6, 126.8, 127.5,
(400 MHz, DMSO-d6): 2.45 (s, 3H, Ar-CH3), 5.41 (s, 2H, N-CH2), 128.0, 128.6, 129.9, 131.1, 131.6, 134.3, 136.9, 138.0, 141.5,
7.24 (t, 1H, J = 7.6 Hz), 7.43 (t, 2H, J = 8.0 Hz), 7.54 (dd, 3H, J = 146.1, 149.6, 152.8, 162.5; ESI-MS (m/z): Calcd. 448.30, found
4.0 Hz, J = 6.8 Hz), 7.62-7.67 (m, 3H), 7.78-7.85 (m, 4H), 8.38 (s, 447.10 (M+); Anal. Calcd. (%) for C23H15Cl2N5O: C, 61.62; H,
1H); 13C NMR (100 MHz, DMSO-d6): 21.5 (Ar-CH3), 52.7 (N- 3.37; N, 15.62. Found: C, 61.69; H, 3.31; N, 15.51.
CH2), 123.9, 124.3, 124.5, 125.8, 126.5, 127.1, 127.3, 127.6, 6.1.2.11.
N-((2,6-dichloroquinolin-3-yl)methyl)-N-phenyl-5-
128.2, 129.7, 129.8, 131.3, 133.3, 137.2, 137.6, 141.4, 145.2, (pyridin-3-yl)-1,3,4-oxadiazol-2-amine (8k
)
148.4, 159.2, 162.9; ESI-MS (m/z): Calcd. 426.90, found 426.40 Yield 76%; brown solid; m.p. 233°C; IR (νmax, cm-1): 1613 (C=N
(M+); Anal. Calcd. (%) for C25H19ClN4O: C, 70.34; H, 4.49; N, str.), 1225 (C-O-C str.), 1096 (N-N str.), 755 (C-Cl str.); H NMR
1
13.12. Found: C, 70.15; H, 4.63; N, 13.25.
(400 MHz, DMSO-d6): 5.48 (s, 2H, N-CH2), 7.27 (t, 1H, J = 7.6
6.1.2.7. N-((2-chloro-6-methoxyquinolin-3-yl)methyl)-N-phenyl- Hz), 7.37-7.58 (m, 3H), 7.68 (d, 2H, J = 8.0 Hz), 7.79-7.84 (m,
5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amine (8g
)
1H), 7.98 (d, 1H, J = 8.8 Hz), 8.15-8.21 (m, 2H), 8.50-8.57 (m,
Yield 72%; light yellow solid; m.p. 226°C; IR (νmax, cm-1): 1615 1H), 8.71 (dd, 1H, J = 1.2 Hz, J = 4.8 Hz), 8.99 (s, 1H); 13C NMR
1
(C=N str.), 1227 (C-O-C str.), 1069 (N-N str.), 742 (C-Cl str.); H (100 MHz, DMSO-d6): 53.0 (N-CH2), 120.8, 124.4, 124.7, 126.7,
NMR (400 MHz, DMSO-d6): 3.84 (s, 3H, Ar-OCH3), 5.44 (s, 2H, 127.2, 128.2, 129.6, 129.8, 130.1, 131.7, 131.8, 132.2, 133.4,
N-CH2), 7.28 (t, 1H, J = 7.2 Hz), 7.30-7.48 (m, 4H), 7.67-7.72 (m, 133.7, 135.2, 136.9, 141.4, 145.1, 146.6, 149.8, 152.0, 162.2;
4H), 7.84 (d, 1H, J = 9.6 Hz), 8.40 (s, 1H), 8.73 (d, 2H, J = 5.6 ESI-MS (m/z): Calcd. 448.30, found 446.80 (M+); Anal. Calcd.
Hz); 13C NMR (100 MHz, DMSO-d6): 53.0 (N-CH2), 56.1 (Ar- (%) for C23H15Cl2N5O: C, 61.62; H, 3.37; N, 15.62. Found: C,
OCH3), 93.2, 110.5, 123.7, 125.8, 126.2, 126.8, 127.0, 127.4, 61.42; H, 3.49; N, 15.69.
128.7, 130.1, 130.5, 137.6, 142.2, 147.8, 150.4, 153.2, 158.0, 6.1.2.12.
N-((2,6-dichloroquinolin-3-yl)methyl)-N,5-diphenyl-
163.2; ESI-MS (m/z): Calcd. 443.89, found 443.40 (M+); Anal. 1,3,4-oxadiazol-2-amine (8l
)
Calcd. (%) for C24H18ClN5O2: C, 64.94; H, 4.09; N, 15.78. Found: Yield 79%; white solid; m.p. 241°C; IR (νmax, cm-1): 1632 (C=N
1
str.), 1229 (C-O-C str.), 1071(N-N str.), 764 (C-Cl str.); H NMR
C, 64.70; H, 4.21; N, 15.91.
6.1.2.8. N-((2-chloro-6-methoxyquinolin-3-yl)methyl)-N-phenyl- (400 MHz, DMSO-d6): 5.41 (s, 2H, N-CH2), 7.27 (t, 1H, J = 7.2
5-(pyridin-3-yl)-1,3,4-oxadiazol-2-amine (8h
)
Hz), 7.45 (t, 2H, J = 8.0 Hz), 7.53-7.58 (m, 3H), 7.68 (d, 2H, J =
Yield 75%; off-white solid; m.p. 242°C; IR (νmax, cm-1): 1659 8.0 Hz), 7.78-7.81 (m, 3H), 7.98 (d, 1H, J = 9.2 Hz), 8.19 (d, 1H, J
(C=N str.), 1231 (C-O-C str.), 1078 (N-N str.), 753 (C-Cl str.); H = 2.0 Hz), 8.51 (s, 1H); 13C NMR (100 MHz, DMSO-d6): 53.2 (N-
1
NMR (400 MHz, DMSO-d6): 3.85 (s, 3H, Ar-OCH3), 5.42 (s, 2H, CH2), 121.4, 123.7, 124.9, 126.0, 127.5, 128.4, 129.7, 131.5,
N-CH2), 7.27 (t, 1H, J = 7.2 Hz), 7.40-7.47 (m, 4H), 7.57 (dd, 1H, 132.0, 132.6, 133.2, 133.7, 135.8, 137.1, 141.9, 145.5, 148.7,
J = 4.8 Hz, J = 8.0 Hz), 7.68 (d, 2H, J = 8.0 Hz), 7.85 (d, 1H, J = 153.5, 163.1; ESI-MS (m/z): Calcd. 447.32, found 446.40 (M+);
8.8 Hz), 8.17 (d, 1H, J = 8.0 Hz), 8.44 (s, 1H), 8.72 (d, 1H, J = 3.6 Anal. Calcd. (%) for C24H16Cl2N4O: C, 64.44; H, 3.61; N, 12.53.
Hz), 8.99 (s, 1H); 13C NMR (100 MHz, DMSO-d6): 52.5 (N-CH2), Found: C, 64.31; H, 3.75; N, 12.45.
55.8 (Ar-OCH3), 90.5, 111.3, 123.1, 124.5, 125.6, 126.0, 126.5, 6.2 Biological evaluation
8 | J. Name., 2012, 00, 1-3
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