Molecules 2011, 16
5137
7.74(d, J = 6.0 Hz, J = 9.0 Hz, 2H, phenyl–4H,6H), 7.40 (d, J = 3.0 Hz, 1H, pyridine–3H),7.25 (d,
J = 9.0 Hz, 2H, phenyl–2H, 6H), 7.16 (q, J = 3.0, 6.0 Hz, 1H, pyridine–5H), 7.00 (s, 2H,
13
phenyl–2H,5H), 3.81 (s, 3H, CH3), 2.79 (d, J = 6.0 Hz, 3H, CH3); C-NMR δ: 173.5 (C), 162.8 (C),
160.3 (C), 160.0 (C), 153.3 (C), 152.6 (CH), 145.6 (CH), 141.7 (C), 135.8 (C), 133.7 (C), 131.9 (CH)
122.2 (CH), 120.9 (CH), 120.9 (CH), 118.9 (CH), 118.9 (CH), 113.6 (CH), 113.1 (CH), 111.3 (CH),
108.6 (CH), 55.6 (CH3), 26.1 (CH3); Anal. Calcd for C22H19N5O3S (%): C, 60.96; H, 4.42; N, 16.16;
found C 60.57, H 4.49, N 16.13.
N-Methyl-4-(4-(5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino)phenoxy)picolinamide (8g). Yield:
1
68%. m.p.: 251–252 °C. MS [MH+] (m/z): 473.0 (M+1); H-NMR δ: 10.95 (s, 1H, –NH), 8.77–8.75
(m, 1H, amide–NH), 8.51 (d, J = 6.0 Hz, 1H, pyridine–6H), 8.11 (d, J = 9.0 Hz, 1H, phenyl–3H),
7.86–7.81 (m, 3H, phenyl-3H,5H, phenyl-5H), 7.62 (q, J = 3.0, 9.0 Hz, 2H, phenyl-6H), 7.39 (d, 1H,
J = 3.0 Hz, pyridine–3H), 7.26 (d, J = 9.0 Hz, 2H, phenyl–2H,6H), 7.16 (q, J = 3.0, 6.0 Hz, 1H,
13
pyridine–5H), 2.79 (d, J = 6.0 Hz, 3H, CH3); C-NMR δ: 173.7 (C), 163.6 (C), 160.9 (C), 151.7 (C),
151.0 (C), 146.2 (CH), 142.4 (C), 136.4 (C), 135.7 (C), 135.0 (C), 133.6 (C), 130.9 (CH), 130.3 (CH)
127.4 (CH), 120.5 (CH), 120.5 (CH), 119.1 (CH), 119.1 (CH), 113.9 (CH), 108.6 (CH), 26.1 (CH3);
Anal. Calcd for C21H15Cl2N5O2S (%): C, 53.40; H, 3.20; N, 14.83; found C 54.07, H 3.31, N 15.01.
N-methyl-4-(4-(5-(2,6-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino)phenoxy)picolinamide (8h). Yield:
1
72%. m.p.: 261–262 °C. MS [MH−] (m/z): 473.8 (M−1); H-NMR δ: 10.90 (s, 1H, –NH), 8.77–8.75
(m, 1H, amide–NH), 8.51 (d, J = 6.0 Hz, 1H, pyridine–6H), 7.84 (d, J = 9.0 Hz, 2H, phenyl–3H,5H),
7.69 (d, J = 9.0 Hz, 2H, phenyl–3H,5H), 7.62–7.57 (m, 1H, phenyl–4H), 7.41 (d, J = 3.0 Hz, 1H,
pyridine–3H), 7.27 (d, J = 9.0 Hz, 2H, phenyl–2H,6H), 7.16 (q, J = 3.0, 6.0 Hz, 1H, pyridine–5H),
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2.80 (d, J = 6.0 Hz, 3H, CH3); C-NMR δ: 173.5 (C), 162.9 (C), 160.3 (C), 151.8 (C), 150.6 (C),
145.5 (CH), 141.7 (C), 138.0 (C), 136.3 (C), 134.7 (C), 134.7 (C), 131.5 (CH), 127.4 (CH), 127.4
(CH) 121.3 (CH), 121.3 (CH), 120.1 (CH), 120.1 (CH), 113.9 (CH), 108.6 (CH), 26.1 (CH3); Anal.
Calcd for C21H15Cl2N5O2S (%): C, 53.40; H, 3.20; N, 14.83; found C 53.67, H 3.34, N 14.89.
N-Methyl-4-(4-(5-(benzo[d][1,3]dioxol-5-yl)-1,3,4-thiadiazol-2-ylamino)phenoxy)picolinamide (8i).
Yield: 47%. m.p.: 243–244 °C. MS [MH+] (m/z): 448.2 (M+1); 1H-NMR δ: 10.65 (s, 1H, -NH), 8.77–8.76
(br, 1H, amide–NH), 8.51 (d, J = 6.0 Hz, 1H, pyridine–6H), 7.79 (d, J = 9.0 Hz, 2H, phenyl–3H,5H),
7.43–7.33 (m, 3H, phenyl–2H, 6H, pyridine–3H), 7.25 (d, J = 9.0 Hz, 2H, phenyl–2H,6H), 7.05 (d, 1H,
J = 9.0 Hz, phenyl–5H), 6.77–6.71 (m, 1H, pyridine–5H), 2.79 (d, J = 6.0 Hz, 3H, CH3); 13C-NMR δ:
174.1 (C), 164.8 (C), 161.0 (C), 152.7 (C), 151.0 (C), 146.6 (C), 146.2 (CH), 145.2 (C), 142.4 (C),
136.4 (C), 123.1 (C), 122.5 (CH), 121.7 (CH), 121.7 (CH), 120.8 (CH), 120.0 (CH), 120.0 (CH), 115.3
(CH), 113.9 (CH), 109.6 (CH), 101.5 (CH2), 26.1 (CH3); Anal. Calcd for C22H17N5O4S (%): C, 59.05;
H, 3.83; N, 15.65; found C 58.73, H 3.81, N 15.59.
N-Methyl-4-(4-(5-(2,5-dimethoxyphenyl)-1,3,4-thiadiazol-2-ylamino)phenoxy)picolinamide (8j). Yield:
1
63%. m.p.: 267–268 °C. MS [MH−] (m/z): 464.7 (M−1); H-NMR δ: 10.57 (s, 1H, –NH), 8.76–8.75
(br, 1H, amide–NH), 8.51 (d, J = 6.0 Hz, 1H, pyridine–6H), 7.82 (d, J = 9.0 Hz, 2H, phenyl–3H,5H),
7.74 (d, J = 3.0 Hz, 1H, phenyl–6H), 7.40 (s, 1H, pyridine–3H), 7.25-7.18 (m, 3H, phenyl–2H,6H,
phenyl–2H), 7.16–7.14 (br, 1H, pyridine–5H), 7.10 (q, J = 3.0 Hz, 6.0 Hz, 1H, pyridine–5H), 2.93