M. A. Dea-Ayuela et al. / Bioorg. Med. Chem. 17 (2009) 7449–7456
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4.1.2.4. 4-Fluoro-N-pyrimidin-2-yl-benzenesulfonamide (4Af)
Yield: 80%; mp: 183–186 °C (lit33 184.5–185 °C); 1H NMR
(300 MHz, DMSO-d6): d = 7.05 (t, J = 4.9, 1H), 7.41 (t, J = 9.0, 2H),
8.03 (dd, J = 9.0, J = 5.0, 2H), 8.50 (d, J = 4.9, 2H), 11.0 (s, 1H, NH);
13C NMR (75 MHz, DMSO-d6): d = 116.1 (CH), 116.5 (CH), 131.0
(CH), 136.9 (C), 157.4 (C), 158.7 (CH), 162.5 (C).
d = 6.86 (td, J = 7.1, J = 0.94, 1H), 7.27 (d, J = 8.8, 1H), 7.81 (td J = 9,
J = 1.8, 1H), 7.94 (dd, J = 7.1, J = 1.8, 1H), 8.09 (d, J = 8.8, 2H), 8.34
(d, J = 8.8, 2H); 13C NMR (75 MHz, DMSO-d6): d = 114.4 (CH),
115.5 (CH), 124.6 (CH), 128.6 (CH), 128.0 (CH), 140.3 (C), 142.8
(CH), 149.0 (C), 149.4 (CH), 154.6 (C); HRMS-EI+: m/z calcd for
C11H9N3O4S: 279.0313, found: 279.0314.
4.1.2.5. 4-Chloro-N-pyrimidin-2-yl-benzenesulfonamide (4Ag)
Yield: 80%; mp: 199–202 °C (lit34 203–204 °C); 1H NMR
(300 MHz, DMSO-d6): d = 7.06 (t, J = 4.9, 1H), 7.63 (d, J = 8.1, 2H),
7.98 (d, J = 8.1, 2H), 8.51 (d, J = 4.9, 2H), 12.03 (s, 1H, NH); 13C
NMR (75 MHz, DMSO-d6): d = 116.1 (CH), 129.4 (CH), 129.8 (CH),
138.1 (C), 139.7 (C), 157.0 (C), 158.7 (CH).
4.1.2.14. 4-Nitro-N-thiazol-2-yl-benzenesulfonamide (4Ca)
Yield: 90%; mp: 263–265 °C (lit40 260–261 °C); 1H NMR
(300 MHz, DMSO-d6): d = 6.95 (d, J = 3.3, 1H), 7.30 (d, J = 3.3, 1H),
8.11 (d, J = 8.5, 2H), 8.40 (d, J = 8.5, 2H); 13C NMR (75 MHz,
DMSO-d6) d: 109.4 (CH), 124.8 (CH), 125.2 (CH), 127.6 (CH),
148.1 (C), 149.6 (C), 169.7 (C).
4.1.2.6. N-(4,6-Dimethyl-pyrimidin-2-yl)-4-nitro-benzenesul-
fonamide (4Aj). Yield: 65%; mp: 218–220 °C (lit.37 215 °C); 1H
NMR (300 MHz, DMSO-d6): d = 2.25 (s, 6H), 6.72 (s, 1H), 8.18 (d,
J = 8.8, 2H), 8.35 (d, J = 8.8, 2H).
4.1.2.15. 4-Chloro-N-thiazol-2-yl-benzenesulfonamide (4Cb)
Yield: 90%; mp: 198–200 °C (lit.34 201–202 °C); 1H NMR
(300 MHz, DMSO-d6): d = 6.80 (d, J = 3.3, 1H); 7.25 (d, J = 3.3, 1H);
7.6 (d, J = 8.5, 2H); 8.80 (d, J = 8.5, 2H); 13C NMR (75 MHz, DMSO-
d6): d = 109.0 (CH); 125.0 (CH); 128.0 (CH); 129.4 (CH); 137.1
(C); 141.6 (C); 169.4 (C).
4.1.2.7. N-(4,6-Dimethyl-pyrimidin-2-yl)-4-chloro-benzenesul-
fonamide (4Ak). Yield: 54%; mp: 185–187 °C (lit.38 181–182 °C);
1H NMR (300 MHz, DMSO-d6): d = 2.25 (s, 6H), 6.75 (s, 1H), 7.62
(d, J = 8.5, 2H), 7.96 (d, J = 8.5, 2H), 12.14 (s, 1H, NH); 13C NMR
(75 MHz, DMSO-d6): d = 22.9 (CH3), 113.1 (CH), 128.8 (CH), 130.2
(C), 130.4 (CH), 137.4 (C), 140.5 (C), 156.2 (C).
4.1.2.16. 4-Nitro-N-5-methyl-thiazol-2-yl-benzenesulfonamide
(4Cc). Yield: 88%; mp: 235–240 °C (lit.41 255 °C); 1H NMR
(300 MHz, DMSO-d6): d = 2.17 (s, 3H), 7.05 (s, 1H), 8.03 (d, J = 8.5,
2H), 8.35 (d, J = 8.5, 2H).
4.1.2.8. 4-Nitro-N-pyrazin-2-yl-benzenesulfonamide (4Ba)
Yield: 86%; mp: 233–237 °C; 1H NMR (300 MHz, DMSO-d6):
d = 8.2 (m, 4H), 8.40 (m, 3H); 13C NMR (75 MHz, DMSO-d6):
d = 124.9 (CH), 129.2 (CH), 133.7 (CH), 139.5 (CH), 142.1 (CH),
145.8 (C), 148.1 (C), 150.3 (C); HRMS-EI+: m/z calcd for
C10H9N4O4S: 281.0344, found: 281.0351.
4.1.2.17. 4-Chloro-N-5-methyl-thiazol-2-yl-benzenesulfon-
amide (4Cd). Yield: 50%; mp: 102–104 °C; 1H NMR (300 MHz,
DMSO-d6): d = 2.06 (s, 3H); 6.33 (s, 1H); 7.58 (d, J = 8.5, 2H); 7.75
(d, J = 8.5, 2H); HRMS-EI+: m/z calcd for C10H9ClN2O2S2: 287.9793,
found: 287.9794.
4.1.2.18. N-5-Methyl-thiazol-2-yl-benzenesulfonamide (4Ce)
Yield: 40%; mp: 149.1–152 °C; 1H NMR (300 MHz, DMSO-d6):
d = 2.15 (s, 3H), 6.46 (s, 1H), 7.61 (m, 3H), 7.85 (d, J = 8.3, 2H);
13C NMR (75 MHz, DMSO-d6): d = 13.7 (CH3); 102.6 (CH); 116.4
(C); 126.1 (CH); 129.2 (CH); 132.2 (CH); 135.0 (C); 165.8 (C).
4.1.2.9. 4-Chloro-N-pyrazin-2-yl-benzenesulfonamide (4Bb)
Yield: 40%; mp: 190–193 °C; 1H NMR (300 MHz, DMSO-d6):
d = 7.67 (d, J = 8.5, 2H), 7.95 (d, J = 8.5, 2H); 8.22 (dd, J = 2.8,
J = 1.5, 1H), 8.22 (d, J = 1.5, 1H); 13C NMR (75 MHz, DMSO-d6):
d = 129.5 (CH), 129.7 (CH), 135.5 (CH), 138.4 (C), 139.2 (CH),
139.3 (C), 142.3 (CH), 148.4 (C), HRMS-EI+: m/z calcd for
C10H9N3O2SCl: 270.0104, found: 270.0107.
4.1.2.19. 4-Nitro-N-4-methyl-thiazol-2-yl-benzenesulfonamide
(4Cf). Yield: 70%; mp: 189.5–193.2 °C (lit.42 197–9 °C). 1H NMR
(300 MHz, DMSO-d6): d = 2.10 (s, 3H), 6.45 (s, 1H), 8.05 (d, J = 8.5,
2H); 8.37 (d, J = 8.5, 2H).
4.1.2.10. N-Pyrazin-2-yl-benzenesulfonamide (4Bc). Yield: 70%;
mp: 204–208 °C; 1H NMR (300 MHz, DMSO-d6): d = 7.60 (m, 3H),
7.93 (d, J = 8, 2H); 8.22 (m, 2H), 8.35 (d, J = 1.3, 1H); 13C NMR
(75 MHz, DMSO-d6): d = 127.4 (CH), 129.6 (CH), 133.6 (CH), 135.2
(CH), 139.2 (CH), 140.2 (C), 142.4 (CH), 148.4 (C); HRMS-FAB+: m/
z calcd for C10H10N3O2S: 236.0493, found: 236.0495.
4.1.2.20. N-4-Methyl-thiazol-2-yl-benzenesulfonamide (4Cg)
Yield: 57%; mp: 164–166 °C (lit.43 161–162 °C). 1H NMR
(300 MHz, DMSO-d6): d = 2.17 (s, 3H); 6.97 (s, 1H); 7.55 (m, 3H);
7.77 (d, J = 8.1, 2H).
4.1.2.11. 4-Nitro-N-pyridin-4-yl-benzenesulfonamide (4Bd)
Yield: 40%; mp: 290–294 °C (lit.39 293–295 °C); 1H NMR
(300 MHz, DMSO-d6): d = 6.97 (d, J = 7.53, 2H), 8.02 (d, J = 7.53,
2H), 8.04 (d, J = 8.86, 2H), 8.31 (d, J = 8.86, 2H); 13C NMR
(75 MHz, DMSO-d6): d = 115.4 (CH), 124.5 (CH), 127.8 (CH), 139.4
(C), 139.5 (CH), 149.1 (C), 150.0 (C).
4.1.2.21. N-(5-Methyl-isoxazol-3-yl)-4-nitro-benzenesulfon-
amide (4Da). Yield: 90%; mp: 190–193 °C (lit.44 194–195 °C); 1H
NMR (300 MHz, DMSO-d6): d = 2.29 (s, 3H), 6.16 (s, 1H), 8.10 (d,
J = 9.2, 2H), 8.42 (d, J = 9.2, 2H); 13C NMR (75 MHz, DMSO-d6) d:
12.4 (CH3), 95.8 (CH), 125.2 (CH), 128.8 (CH), 144.9 (C), 149.5 (C),
157.4 (C), 171.0 (C).
4.1.2.12. 4-Nitro-N-pyridin-3-yl-benzenesulfonamide (4Be)
Yield: 88%; mp: 240–243 °C; 1H NMR (300 MHz, DMSO-d6):
d = 7.33 (dd, J = 8.2, J = 4.8, 1H), 7.51 (ddd, J = 8.2, J = 2.6, J = 1.5,
1H), 8.02 (d, J = 8.85, 2H), 8.31 (m, 2H), 8.37 (d, J = 8.85, 2H), 10.9
(s, 1H, NH); 13C NMR (75 MHz, DMSO-d6): d = 124.5 (CH), 125.2
(CH), 128.6 (CH), 128.7 (CH), 134.0 (C), 142.6 (CH), 144.7 (C),
146.3 (CH), 150.3 (C); HRMS-EI+: m/z calcd for C11H9N3O4S:
279.0313, found: 279.0299.
4.1.2.22. N-(5-Methyl-isoxazol-3-yl)-4-chlorobenzenesulfona-
mide (4Db). Yield: 60%; mp: 158.5–159.9 °C; 1H NMR (300 MHz,
DMSO-d6): d = 2.29 (s, 3H); 6.14 (s, 1H); 7.70 (d, J = 8.8, 2H); 7.85
(d, J = 8.8, 2H), 11.5 (br s, 1H, NH); 13C NMR (75 MHz, DMSO-d6)
d: 12.4 (CH3), 95.8 (CH), 129.0 (CH), 129.9 (CH), 138.6 (C), 138.7
(C), 149.5 (C), 157.6 (C), 171.0 (C); HRMS-EI+: m/z calcd for
C10H9N2O3SCl: 272.0022, found: 282.0019.
4.1.2.23. N-(5-Methyl-isoxazol-3-yl)-benzenesulfonamide (4Dc)
Yield: 90%; mp: 105–108 °C (lit.45 112.5 °C); 1H NMR (300 MHz,
DMSO-d6): d = 2.29 (s, 3H); 6.14 (s, 1H); 7.62 (m, 3H); 7.87 (d,
4.1.2.13. 4-Nitro-N-pyridin-2-yl-benzenesulfonamide (4Bf)
Yield: 63%; mp: 185–186 °C; 1H NMR (300 MHz, DMSO-d6):