6904
D. Takaya et al. / Bioorg. Med. Chem. 19 (2011) 6892–6905
1H NMR (300 MHz, CDCl3) d 10.22 (s, 1H), 8.26 (d, J = 8.7 Hz,
MS calcd. for C24H17N5O10 (M+H)+ 536.1, found 535.8.
2H), 7.63 (d, J = 8.7 Hz, 2H), 7.42 (s, 1H), 6.71 (s, 1H), 5.31 (s, 2H),
3.94 (s, 3H), 2.96 (q, J = 7.5 Hz, 2H), 1.23 (t, J = 7.5 Hz, 3H).
Acknowledgments
4.3.2.14.
phenyl)methoxy]phenyl]methylideneamino]-5-nitro-1-benzo-
furan-2-carboxamide). Compound 16 (100 mg, 0.388 mmol)
Compound
10
(N-[(E)-[3-methoxy-4-[(4-nitro-
This work was supported by Health and Labor Sciences Re-
search Grants for Research on Hepatitis, as well as by Grants-in-
Aid for research on hepatitis and BSE, from the Ministry of Health,
Labor and Welfare and by a contract research fund for the Program
of Funding Research Centers for Emerging and Reemerging Infec-
tious Diseases, from the Ministries of Education, Culture, Sports,
Science, and Technology, Japan. This work was supported by the
RIKEN Structural Genomics/Proteomics Initiative (RSGI), the Na-
tional Project on Protein Structural and Functional Analyses, and
the Targeted Proteins Research Program (TPRP), the Ministry of
Education, Culture, Sports, Science and Technology (MEXT) of Ja-
pan. We thank Dr. Shunta Sasaki, from Structure Based Drug De-
sign Research, for the MS data analysis.
was suspended in toluene, and compound 19a (122 mg,
0.425 mmol) and sodium acetate (36 mg, 0.44 mmol) were added.
The resultant solution was stirred at 80 °C for 20 h. After cooling in
air, the solution was filtered, and washed with water and toluene
to give compound 10 (114 mg, 0.232 mmol, 60% yield, 100%
purity).
1H NMR (300 MHz, DMSO-d6) d 8.83 (d, J = 2.4 Hz, 1H), 8.44 (s,
1H), 8.35 (dd, J = 9.0 Hz, J = 2.4 Hz, 1H), 7.27 (d, J = 8.7 Hz, 2H), 7.95
(d, J = 9.0 Hz, 1H), 7.91 (s, 1H), 7.73 (d, J = 8.7 Hz, 2H), 7.40 (s, 1H),
7.26–7.10 (m, 2H), 5.34 (s, 2H), 3.87 (s, 3H).
MS calcd. for C24H18N4O8 (M+H)+ 491.11, found 490.8.
Supplementary data
4.3.2.15. Compound 11 (N-[(E)-[5-methoxy-2-methyl-4-[(4-
nitrophenyl)methoxy]phenyl]methylideneamino]-5-nitro-1-
Supplementary data associated with this article can be found, in
benzofuran-2-carboxamide).
Compound
16
(116 mg,
0.450 mmol) was suspended in toluene (3 mL), and compound
19d (149 mg, 0.495 mmol) and sodium acetate (41 mg, 0.50 mmol)
were added. The resultant solution was stirred at room tempera-
ture for 1 h, at 80 °C for 5 h and at 100 °C for 4 h. After cooling in
air, the solution was filtered and suspended in dimethoxyethane
at 80 °C for 1 h. The mixture was then cooled in air, filtered and
washed with dimethoxyethane to give compound 11 (122 mg,
0.242 mmol, 54% yield, 95.5% purity).
References and notes
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1H NMR (300 MHz, DMSO-d6) d 8.82 (s, 1H), 8.80 (s, 1H), 8.36
(d, J = 9.3 Hz, 1H), 8.27 (d, J = 7.8 Hz, 2H), 7.95 (d, J = 9.0 Hz, 1H),
7.90 (s, 1H), 7.73 (d, J = 7.8 Hz, 2H), 7.45 (s, 1H), 6.97 (s, 1H), 5.32
(s, 2H), 3.83 (s, 3H), 2.71 (q, J = 7.5 Hz, 2H), 1.61 (t, J = 7.5 Hz,
3H). MS calcd. for C26H22N4O8 (M+H)+ 519.14, found 518.7.
4.3.2.17. Compound 13 (N-[(E)-[3-methoxy-5-nitro-4-[(4-nitro-
phenyl)methoxy]phenyl]methylideneamino]-5-nitro-1-benzo-
furan-2-carboxamide).
Compound 16 (100 mg, 0.388 mmol)
was suspended in toluene (2 mL), and compound 19c (142 mg,
0.427 mmol) and sodium acetate (35 mg, 0.43 mmol) were added.
The resultant solution was stirred at room temperature for 15 h
and at 80 °C for 5 h. After cooling in air, the obtained solution
was filtered and washed with water and toluene to give compound
13 (148 mg, 0.276 mmol, 71% yield, 95.9% purity).
1H NMR (300 MHz, DMSO-d6) d 8.80 (d, J = 2.1 Hz, 1H), 8.53 (s,
1H), 8.33 (dd, J = 9.0 Hz, J = 2.1 Hz, 1H), 8.26 (d, J = 9.0 Hz, 2H), 7.94
(d, J = 9.0 Hz, 1H), 7.92 (s, 1H), 7.78 (s, 1H), 7.73 (s, 1H), 7.70 (d,
J = 9.0 Hz, 2H), 5.31 (s, 2H), 4.00 (s, 3H).
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