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5.1.31. N-(2,40-Dimethoxybiphenyl-4-yl)-6-methoxy-2-
naphthamide (10r)
5.1.37. N-(30-Methoxybiphenyl-4-yl)naphthalene-2-
sulfonamide (11c)
Prepared by coupling of 35i with 22 using the procedure de-
scribed for the preparation of 10a. White powder, Yield 58%, mp
224–225 °C; 1H NMR (DMSO-d6) d 3.78 (s, 6H), 3.92 (s, 3H), 6.95
(d, 2H, J = 8.3 Hz), 7.24–7.28 (m, 2H), 7.41 (br s, 3H), 7.53 (d, 1H,
J = 8.1 Hz), 7.65 (br s, 1H), 7.94 (d, 1H, J = 8.2 Hz), 8.00 (d, 2H,
J = 8.9 Hz), 8.52 (s, 1H), 10.39 (s, 1H); HPLC (214 nm) tr 29.2 min,
100%; LC–MS (214 nm) tr 19.0 min, 100%; MS (ESI) m/z 414 (M+H)+.
Prepared by treatment of 35b with 38 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 49%, mp
101–102 °C; 1H NMR (DMSO-d6) d 3.74 (s, 3H), 6.84 (dd, 1H,
J = 8.2 Hz), 7.04 (s, 1H), 7.08 (d, 1H, J = 7.8 Hz), 7.19 (d, 2H,
J = 8.5 Hz), 7.27 (t, 1H, J = 7.9 Hz), 7.50 (d, 2H, J = 7.5 Hz), 7.61–
7.69 (m, 2H), 7.80 (dd, 1H, J = 8.7 Hz), 7.98 (d, 1H, J = 7.9 Hz),
8.08 (d, 1H, J = 8.8 Hz), 8.12 (d, 1H, J = 8.0 Hz), 8.46 (s, 1H), 10.5
(s, 1H); HPLC (214 nm) tr 28.2 min, 100%; LC–MS (214 nm) tr
18.6 min, 100%; MS (ESI) m/z 390 (M+H)+.
5.1.32. Methyl 40-(6-chloro-2-naphthamido)biphenyl-3-
carboxylate (10s)
Prepared by coupling of 32a with 37 using the procedure de-
scribed for the preparation 10a. Brown powder, Yield 22%, mp
210–211 °C; 1H NMR (DMSO-d6) d 3.89 (s, 3H), 7.59–7.65 (m,
3H), 7.74 (d, 3H, J = 8.5 Hz), 7.91–7.98 (m, 4H), 8.07 (dd, 1H,
J = 8.6 Hz), 8.15 (d, 1H, J = 8.7 Hz), 8.20 (s, 1H), 8.62 (s, 1H), 10.60
(s, 1H); HPLC (214 nm) tr 31.8 min, 95%; LC–MS (214 nm) tr
21.9 min, 88%; MS (ESI) m/z 416 (M+H)+.
5.1.38. N-(Biphenyl-4-yl)-6-methoxynaphthalene-2-
sulfonamide (11d)
Prepared by treatment of 35a with 39 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 56%, mp
180–181 °C; 1H NMR (DMSO-d6) d 3.87 (s, 3H), 7.19–7.40 (m,
7H), 7.49–7.53 (m, 4H), 7.73 (dd, 1H, J = 8.7 Hz), 7.95 (d, 1H,
J = 8.8 Hz), 8.03 (d, 1H, J = 9.0 Hz), 8.38 (s, 1H), 10.45 (s, 1H); HPLC
(214 nm) tr 28.0 min, 100%; LC–MS (214 nm) tr 18.4 min, 100%; MS
(ESI) m/z 390 (M+H)+.
5.1.33. Methyl 40-(6-bromo-2-naphthamido)biphenyl-3-
carboxylate (10t)
5.1.39. Methyl 40-(6-methoxynaphthalene-2-
sulfonamido)biphenyl-3-carboxylate (11e)
Prepared by coupling of 32a with 20 using the procedure de-
scribed for the preparation of 10a. Brown powder, Yield 33%, mp
231–232 °C; 1H NMR (DMSO-d6) d 3.89 (s, 3H), 7.61 (t, 1H,
J = 7.8 Hz), 7.75 (d, 3H, J = 8.6 Hz), 7.92–7.99 (m, 4H), 8.04–8.09
(m, 3H), 8.21 (s, 1H), 8.30 (s, 1H), 8.61 (s, 1H), 10.61 (s, 1H); HPLC
(214 nm) tr 32.4 min, 100%; LC–MS (214 nm) tr 21.6 min, 100%; MS
(ESI) m/z 462 (M+H)+.
Prepared by treatment of 32a with 39 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 34%, mp
156–157 °C; 1H NMR (DMSO-d6) d 3.84 (s, 3H), 3.87 (s, 3H), 7.22
(d, 2H, J = 8.5 Hz), 7.25 (dd, 1H, J = 9.0, 9.1 Hz), 7.38 (s, 1H), 7.53
(t, 3H, J = 8.7 Hz), 7.74 (dd, 1H, J = 8.7 Hz), 7.81 (d, 1H, J = 7.9 Hz),
7.86 (d, 1H, J = 7.7 Hz), 7.94 (d, 1H, J = 8.8 Hz), 8.01–8.05 (m, 2H),
8.38 (s, 1H), 10.50 (s, 1H); HPLC (214 nm) tr 27.6 min, 100%; LC–
MS (214 nm) tr 18.6 min, 100%; MS (ESI) m/z 448 (M+H)+.
5.1.34. Methyl 40-(6-amino-2-naphthamido)biphenyl-3-
carboxylate (10u)
Prepared by coupling of 32a with 21 using the procedure de-
scribed for the preparation of 10a. Brown powder, Yield 40%, mp
233–234 °C; 1H NMR (DMSO-d6) d 3.90 (s, 3H), 5.7 (s, 2H), 6.85
(s, 1H), 7.01 (dd, 1H, J = 8.7 Hz), 7.57–7.64 (m, 2H), 7.73 (dd, 3H,
J = 8.8 Hz), 7.83–8.09 (m, 5H), 8.20 (s, 1H), 8.34 (s, 1H), 10.60 (s,
1H); HPLC (214 nm) tr 20.8 min, 83%; LC–MS (214 nm) tr
17.7 min, 79%; MS (ESI) m/z 397 (M+H)+.
5.1.40. 40-(6-Methoxynaphthalene-2-sulfonamido)biphenyl-3-
carboxamide (11f)
Prepared by treatment of 32c with 39 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 28%, mp
229–230 °C; 1H NMR (DMSO-d6) d 3.86 (s, 3H), 7.20 (d, 2H,
J = 8.6 Hz), 7.26 (dd, 1H, J = 9.0 Hz), 7.39 (s, 1H), 7.44 (t, 1H,
J = 7.7 Hz), 7.56 (d, 2H, J = 8.6 Hz), 7.67 (d, 1H, J = 7.8 Hz), 7.78 (t,
1H, J = 7.8 Hz), 7.95 (d, 1H, J = 8.8 Hz), 8.02 (t, 3H, J = 9.0 Hz), 8.39
(s, 1H), 10.48 (s, 1H); HPLC (214 nm) tr 21.2 min, 93%; LC–MS
(214 nm) tr 16.0 min, 93%; MS (ESI) m/z 433 (M+H)+.
5.1.35. Methyl 40-(naphthalene-2-sulfonamido)biphenyl-3-
carboxylate (11a)
To a solution of 32a (230 mg, 1 mmol) in 3 mL pyridine was
added 38 (230 mg, 1 mmol) and the reaction mixture was stirred
overnight. The mixture was acidified to pH 2 and then extracted
with EtOAc (2 ꢀ 75 mL), washed with water and brine, dried
(Na2SO4), filtered, and concentrated to afford brown solid which
was washed with methanol to provide 220 mg of 11a. White pow-
der, Yield 53%, mp 172–173 °C; 1H NMR (DMSO-d6) d 3.83 (s, 3H),
7.24 (d, 2H, J = 8.5 Hz), 7.51 (d, 1H, J = 7.8 Hz), 7.55 (d, 2H,
J = 8.5 Hz), 7.62–7.69 (m, 2H), 7.80 (d, 2H, J = 8.4 Hz), 7.86 (d, 1H,
J = 7.7 Hz), 7.98 (d, 1H, J = 7.8 Hz), 8.05–8.14 (m, 3H), 8.47 (s, 1H),
10.5 (s, 1H); HPLC (214 nm) tr 27.8 min, 100%; LC–MS (214 nm) tr
19.4 min, 100%; MS (ESI) m/z 418 (M+H)+.
5.1.41. 6-Methoxy-N-(30-(trifluoromethyl)biphenyl-4-
yl)naphthalene-2-sulfonamide (11g)
Prepared by treatment of 35d with 39 using the procedure de-
scribed for the preparation of 11a. Brown powder, Yield 53%, mp
162–163 °C; 1H NMR (DMSO-d6) d 3.87 (s, 3H), 7.22 (d, J = 8.7 Hz,
2H), 7.26 (dd, 1H, J = 9.0 Hz), 7.39 (s, 1H), 7.58–7.64 (m, 4H), 7.74
(dd, 1H, J = 8.7 Hz), 7.82–7.86 (m, 2H), 7.95 (d, 1H, J = 8.8 Hz),
8.03 (d, 1H, J = 9.0 Hz), 8.40 (s, 1H), 10.54 (s, 1H); HPLC (214 nm)
tr 30.0 min, 96%; LC–MS (214 nm) tr 19.8 min, 92%; MS (ESI) m/z
458 (M+H)+.
5.1.42. N-(30-Fluorobiphenyl-4-yl)-6-methoxynaphthalene-2-
sulfonamide (11h)
5.1.36. Methyl 40-(naphthalene-2-sulfonamido)biphenyl-4-
carboxylate (11b)
Prepared by treatment of 35e with 39 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 30%, mp
161–162 °C; 1H NMR (DMSO-d6) d 3.87 (s, 3H), 7.10 (t, 1H,
J = 7.2 Hz), 7.20 (d, 2H, J = 8.6 Hz), 7.26 (d, 1H, J = 9.0 Hz), 7.35–
7.41 (m, 4H), 7.54 (d, 2H, J = 8.6 Hz), 7.74 (dd, 1H, J = 8.7 Hz),
7.94 (d, 1H, J = 8.7 Hz), 8.02 (d, 1H, J = 9.0 Hz), 8.38 (s, 1H), 10.47
(s, 1H); HPLC (214 nm) tr 28.4 min, 95%; LC–MS (214 nm) tr
18.9 min, 96%; MS (ESI) m/z 406 (MꢁH)ꢁ.
Prepared by treatment of 32b with 38 using the procedure de-
scribed for the preparation of 11a. White powder, Yield 34%, mp
189–190 °C; 1H NMR (DMSO-d6) d 3.82 (s, 3H), 7.24 (d, 2H,
J = 8.6 Hz), 7.59–7.70 (m, 6H), 7.80 (dd, 1H, J = 8.7 Hz), 7.93 (d,
2H, J = 8.4 Hz), 7.98 (d, 1H, J = 7.9 Hz), 8.10 (dd, 2H, J = 8.8,
7.9 Hz), 8.49 (s, 1H), 10.60 (s, 1H); HPLC (214 nm) tr 27.6 min,
100%; LC–MS (214 nm) tr 18.4 min, 100%; MS (ESI) m/z 418 (M+H)+.