m.p.: 135~137°C. EI-MS (m/z): 413.3 [M]+. 1H-NMR (400
MHz, DMSO) δ 8.17 (d, J = 8.0 Hz, 1H), 7.91 (dd, J = 8.0
Hz, 1H), 7.80 (d, J = 8.0 Hz, 2H), 7.60 (dd, J = 8.0 Hz,
1H), 7.52 (s, 1H), 7.38 - 7.25 (m, 1H), 7.17 (s, 3H), 6.84
(d, J = 8.0 Hz, 1H), 4.08 (d, J = 8.0 Hz, 2H), 2.79 (d, J =
8.0 Hz, 2H), 1.88 (d, J = 8.0 Hz, 4H), 0.98 (dd, J = 8.0 Hz,
6H).
1H), 7.19 (t, J = 4.0 Hz, 2H), 7.14 (s, 1H), 6.83 (dd, J = 8.0
Hz, 1H), 4.08 (t, J = 4.0 Hz, 2H), 3.59 (s, 4H), 2.41 (s,
6H), 1.92 (s, 2H).
N-{3-chloro-4-[3-(dimethylamino)propoxy]phenyl}-3'-
hydroxybiphenyl-3-carboxamide (19a)
1
m.p.: 152-155°C. EI-MS (m/z): 422.9 [M]+. H-NMR (400
MHz, DMSO) δ 8.17 (s, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.80
(d, J = 8.0 Hz, 1H), 7.69 (d, J = 8.0 Hz, 2H), 7.59 (t, J =
4.0 Hz, 1H), 7.30 (t, J = 4.0 Hz, 1H), 7.22 - 7.11 (m, 2H),
6.95 (d, J = 8.0 Hz, 2H), 6.84 (d, J = 8.0 Hz, 1H), 4.05 (t, J
= 4.0 Hz, 2H), 2.65 (t, J = 4.0 Hz, 2H), 2.24 (s, 6H), 1.89
(s, 2H).
N-[3-fluoro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3'-
hydroxybiphenyl-3-carboxamide (18d)
1
m.p.: 110-113°C. EI-MS (m/z): 420.2 [M]+. H-NMR (400
MHz, DMSO) δ 8.17 (s, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.84
- 7.76 (m, 2H), 7.60 (t, J = 4.0 Hz, 1H), 7.53 (d, J = 8.0
Hz, 1H), 7.30 (t, J = 4.0 Hz, 1H), 7.25 - 7.16 (m, 2H), 7.15
(s, 1H), 6.86 (dd, J = 8.0 Hz, 1H), 6.40 (dd, J = 8.0 Hz,
1H), 4.21 (t, J = 4.0 Hz, 2H), 3.00 (s, 2H), 2.73 (s, 4H),
1.75 (s, 4H).
N-{3-chloro-4-[2-(dimethylamino)ethoxy]phenyl}-3'-
hydroxybiphenyl-3-carboxamide (19b)
1
m.p.: 166-168°C. EI-MS (m/z): 375.9 [M]+. H-NMR (400
MHz, DMSO) δ 8.17 (s, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.80
(d, J = 8.0 Hz, 1H), 7.69 (d, J = 8.0 Hz, 2H), 7.59 (t, J =
4.0 Hz, 1H), 7.30 (t, J = 4.0 Hz, 1H), 7.21 - 7.12 (m, 2H),
6.95 (d, J = 8.0 Hz, 2H), 6.84 (d, J = 8.0 Hz, 1H), 4.05 (t, J
= 4.0 Hz, 2H), 2.65 (t, J = 4.0 Hz, 2H), 2.24 (s, 6H).
N-{3-chloro-4-[2-(diethylamino)ethoxy]phenyl}-3'-
hydroxybiphenyl-3-carboxamide (19c)
N-[3-fluoro-4-(2-piperidin-1-ylethoxy)phenyl]-3'-
hydroxybiphenyl-3-carboxamide (18e)
1
m.p.: 169-172°C. EI-MS (m/z): 434.1 [M]+. H-NMR (400
MHz, DMSO) δ 7.92 (d, J = 8.0 Hz, 1H), 7.82 (d, J = 8.0
Hz, 1H), 7.76 (dd, J = 8.0 Hz, 1H), 7.61 (t, J = 4.0 Hz,
1H), 7.50 (d, J = 8.0 Hz, 1H), 7.31 (t, J = 4.0 Hz, 1H), 7.21
- 7.16 (m, 2H), 7.14 (d, J = 8.0 Hz, 1H), 6.83 (dd, J = 8.0
Hz, 1H), 4.07 (t, J = 4.0 Hz, 2H), 3.40 (s, 2H), 2.42 - 2.32
(m, 2H), 2.16 (s, 6H), 1.87 (dd, J = 8.0 Hz, 2H).
m.p.: 208~210°C. EI-MS (m/z): 438.2 [M]+. 1H-NMR (400
MHz, DMSO) δ 8.18 (s, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.80
(d, J = 8.0 Hz, 1H), 7.74 (d, J = 8.0 Hz, 2H), 7.64 - 7.56
(m, 1H), 7.30 (t, J = 4.0 Hz, 1H), 7.21 - 7.14 (m, 2H), 6.99
(d, J = 8.0 Hz, 2H), 6.84 (dd, J = 8.0 Hz, 1H), 4.27 (s, 2H),
3.25 (s, 2H), 2.99 (s, 4H), 1.17 (t, J = 4.0 Hz, 6H).
N-[3-chloro-4-(2-pyrrolidin-1-ylethoxy)phenyl]-3'-
hydroxybiphenyl-3-carboxamide (19d)
N-[3-fluoro-4-(2-morpholin-4-ylethoxy)phenyl]-3'-
hydroxybiphenyl-3-carboxamide (18f)
1
m.p.: 158-160°C. EI-MS (m/z): 436.2 [M]+. H-NMR (400
MHz, DMSO) δ 8.15 (s, 1H), 7.92 (d, J = 8.0 Hz, 1H), 7.82
(d, J = 8.0 Hz, 1H), 7.76 (dd, J = 8.0 Hz, 1H), 7.61 (t, J =
4.0 Hz, 1H), 7.51 (t, J = 4.0 Hz, 1H), 7.31 (t, J = 4.0 Hz,
1H), 7.20 (dd, J = 8.0 Hz, 2H), 7.13 (s, 1H), 6.83 (dd, J =
8.0 Hz, 1H), 4.16 (t, J = 4.0 Hz, 2H), 3.61 - 3.55 (m, 4H),
3.36 (s, 2H), 2.71 (t, J = 4.0 Hz, 2H), 2.49 (s, 2H).
N-[3-fluoro-4-(3-morpholin-4-ylpropoxy)phenyl]-3'-
hydroxybiphenyl-3-carboxamide (18g)
1
m.p.: 145-147°C. EI-MS (m/z): 420.2 [M]+. H-NMR (400
MHz, DMSO) δ 8.17 (s, 1H), 7.93 (d, J = 8.0 Hz, 1H), 7.81
(d, J = 8.0 Hz, 1H), 7.72 (d, J = 8.0 Hz, 2H), 7.60 (t, J =
4.0 Hz, 1H), 7.30 (t, J = 4.0 Hz, 1H), 7.22 - 7.11 (m, 2H),
6.99 (d, J = 8.0 Hz, 2H), 6.83 (d, J = 8.0 Hz, 1H), 4.20 (s,
2H), 3.18 (s, 2H), 2.94 (s, 4H), 1.83 (s, 4H).
1
m.p.: 162-164°C. EI-MS (m/z): 450.0 [M]+. H-NMR (400
N-[3-chloro-4-(2-piperidin-1-ylethoxy)phenyl]-3'-
MHz, DMSO) δ 8.16 (s, 1H), 7.92 (d, J = 8.0 Hz, 1H), 7.82
(d, J = 8.0 Hz, 1H), 7.77 (dd, J = 8.0 Hz, 1H), 7.61 (t, J =
4.0 Hz, 1H), 7.51 (d, J = 8.0 Hz, 1H), 7.31 (t, J = 4.0 Hz,
hydroxybiphenyl-3-carboxamide (19e)
m.p.: 152-154°C. EI-MS (m/z): 450.3 [M]+. H-NMR (400
1
MHz, DMSO) δ 8.18 (s, 1H), 7.94 (d, J = 8.0 Hz, 1H), 7.81
8