M. Kainuma et al. / Bioorg. Med. Chem. 15 (2007) 2587–2600
2599
1
mp 112–115 ꢁC; H NMR (500 MHz, CDCl3) d 8.34 (s,
7.40 (m, 1H), 7.33 (t, J = 8.5 Hz, 1H), 6.82 (d, J = 2.5 Hz,
1H), 6.77 (dd, J = 2.5, 8.5 Hz, 1H), 4.78 (s, 2H), 3.92 (s,
3H), 1.52 (s, 9H); FAB: MS m/z; 587 (M+H)+.
1H), 8.16 (d, J = 6.4 Hz, 2H), 8.11 (d, J = 8.4 Hz, 1H),
8.01 (d, J = 8.9 Hz, 1H), 7.93–7.89 (m, 4H), 7.79 (d,
J = 8.9 Hz, 1H), 7.62–7.56 (m, 2H), 7.51–7.46 (m, 3H),
7.40 (t, J = 8.9 Hz, 1H), 6.87 (d, J = 2.5 Hz, 1H), 6.83
(dd, J = 2.5, 8.5 Hz, 1H), 5.02 (s, 2H); FAB: MS m/z;
643; HRMS (FAB, MH+) calcd for C34H22Cl3N2O5
643.0594, found 643.0604.
5.1.64. 3-{5-tert-Butyl-3-(2,6-dichlorophenyl)isoxazol-4-
ylmethoxy]-2-chlorobenzoylamino}benzooic acid (15f).
This compound was prepared from methyl 3-{5-tert-bu-
tyl-3-(2,6-dichlorophenyl)isoxazol-4-ylmethoxy]-2-chlo-
robenzoylamino}benzoate by means of a procedure
1
5.1.59. 4-[5-Biphenyl-4-yl-3-(2,6-dichlorophenyl)isoxazol-
4-ylmethoxy]-2-chlorobenzoic acid (12g). This compound
was prepared from 4-[5-biphenyl-4-yl-3-(2,6-dichloro-
phenyl)isoxazol-4-ylmethoxy]-2-chlorobenzaldehyde
by means of a procedure similar to that used for 2-
chloro-4-[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-
similar to that used for 15a: mp 100–104 ꢁC; H NMR
(500 MHz, CDCl3) d 8.16–8.09 (m, 2H), 7.89 (d,
J = 8.9 Hz, 1H), 7.79 (d, J = 8.5 Hz, 1H), 7.49 (t,
J = 8.1 Hz, 1H), 7.42–7.40 (m, 2H), 7.34 (t, J = 8.9 Hz,
1H), 6.82 (d, J = 2.5 Hz, 1H), 6.78 (dd, J = 2.5, 8.9 Hz,
1H), 4.78 (s, 2H), 1.52 (s, 9H); MS (FAB, MH+) m/z
573; HRMS (FAB, MH+) calcd for C28H24Cl3N2O5
573.0751, found 573.0775.
1
ylmethoxy]benzoic acid; H NMR (500 MHz, CDCl3) d
7.95 (d, J = 8.9 Hz, 1H), 7.90 (d, J = 8.5 Hz, 2H), 7.77
(d, J = 8.5 Hz, 2H), 7.65 (d, J = 7.7 Hz, 2H), 7.50–7.37
(m, 6H), 6.88 (d, J = 2.5 Hz, 1H), 6.75 (dd, J = 2.5,
8.9 Hz, 1H), 4.97 (s, 2H); FAB: MS m/z; 550 (M+H)+.
Acknowledgments
5.1.60. Methyl 3-{4-biphenyl-4-yl-3-(2,6-dichlorophe-
nyl)isoxazol-4-ylmethoxy]-2-chlorobenzoylamino}benzo-
ate (13g). This compound was prepared from 12g by
The work described in this paper was partially support-
ed by Grants-in-Aid for Scientific Research from The
Ministry of Education, Culture, Sports, Science and
Technology, Japan, and the Japan Society for the Pro-
motion of Science.
1
means of a procedure similar to that used for 11a; H
NMR (500 MHz, CDCl3) d 8.11 (s, 2H), 8.02 (d,
J = 7.7 Hz, 1H), 7.92 (d, J = 8.5 Hz, 2H), 7.83 (d,
J = 8.5 Hz, 2H), 7.78 (d, J = 8.5 Hz, 1H), 7.66 (d,
J = 7.3 Hz, 2H), 7.50–7.38 (m, 7H), 6.85 (d, J = 2.5 Hz,
1H), 6.81 (dd, J = 2.5, 8.5 Hz, 1H), 4.97 (s, 2H), 3.93
(s, 3H); FAB: MS m/z; 683 (M+H)+.
References and notes
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5.1.61. 3-{4-Biphenyl-4-yl-3-(2,6-dichlorophenyl)-isoxazol-
4-ylmethoxy]-2-chlorobenzoylamino}benzoate (15h). This
compound was prepared from methyl 3-{2-chloro-4-[3-
(2,6-dichlorophenyl)-5-naphthalen-2-ylisoxazol-4-ylmeth-
oxy]benzoylamino}benzoate by means of a procedure sim-
ilar to that used for15a: mp 115–117 ꢁC; 1H NMR
(500 MHz, CDCl3) d 8.16 (d, J = 9.4 Hz, 2H), 8.10 (d,
J = 8.7 Hz, 1H), 7.93–7.89 (m, 3H), 7.78 (d, J = 8.5 Hz,
2H), 7.66 (d, J = 8.5 Hz, 2H), 7.51–7.45 (m, 5H), 7.42–
7.438 (m, 2H), 6.85 (d, J = 2.5 Hz, 1H), 6.81 (dd, J = 2.5,
8.5 Hz, 1H), 4.97 (s, 2H); FAB: MS m/z; 669 (M+H)+;
HRMS (FAB, MH+) calcd for C36H24Cl3N2O5 669.0751,
found 669.0759.
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5.1.62. 4-[5-tert-Butyl-3-(2,6-dichlorophenyl)isoxazol-4-
ylmethoxy]-2-chlorobenzoic acid (12d). This compound
was prepared from 4-[5-tert-butyl-3-(2,6-dichlorophe-
nyl)isoxazol-4-ylmethoxy]-2-chlorobenzaldehyde by means
of a procedure similar to that used for 2-chloro-4-[3-(2,6-
dichlorophenyl)-5-isopropylosoxazol-4-ylmethoxy]benzoic
1
acid; H NMR (500 MHz, CDCl3) d 7.95 (d, J = 9.0 Hz,
1H), 7.40 (d, J = 8.9 Hz, 2H), 7.32 (t, J = 8.9 Hz, 1H),
6.84 (d, J = 2.5 Hz, 1H), 6.71 (dd, J = 2.5, 9.0 Hz, 1H),
4.78 (s, 2H), 1.51 (s, 9H); FAB: MS m/z; 454 (M+H)+.
5.1.63. Methyl 3-{5-tert-butyl-3-(2,6-dichlorophenyl)iso-
xazol-4-ylmethoxy]-2-chlorobenzoylamino}benzoate (13d).
This compound was prepared from 12d by means of a pro-
cedure similar to that used for 11a; 1H NMR (500 MHz,
CDCl3) d 8.12 (d, J = 15.3 Hz, 2H), 8.02 (d, J = 8.1 Hz,
1H), 7.84–7.76 (m, 1H), 7.45 (t, J = 8.1 Hz, 1H), 7.42–