T. Nittoli et al. / European Journal of Medicinal Chemistry 45 (2010) 1379–1386
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2H), 4.08 (s, 3H), 4.03 (m, 2H), 3.97 (s, 3H), 2.93 (m, 1H), 2.73 (m,
1H). HRMS: calcd for C28H27N5O3 þ Hþ, 482.21867; found (ESI-
FTMS, [M þ H]1þ), 482.22024.
HRMS: calcd for C28H26ClN5O3 þ Hþ, 516.17969; found (ESI-
FTMS, [M þ H]1þ), 516.1801.
5.3.37. 2-(5-{[(2S)-2-Amino-3-(3-chlorophenyl)propyl]oxy}pyridin-
5.3.30. 2-(5-{[(2S)-2-Amino-3-(4-
3-yl)-8,9- dimethoxybenzo[c]-2,7-naphthyridin-4-amine (9q)
fluorophenyl)propyl]oxy}pyridin-3-yl)-8,9- dimethoxybenzo[c]-2,7-
naphthyridin-4-amine (9j)
1H NMR (400 MHz, DMSO-d6)
d 9.49 (s, 1H), 9.25 (s, 1H), 8.42 (s,
1H), 8.37 (s, 1H), 8.18 (m, 2H), 7.52 (s, 1H), 7.46 (s, 1H), 7.35 (m, 4H),
4.32 (m, 1H), 4.14 (m, 1H), 4.08 (s, 3H), 3.98 (s, 3H), 3.90 (m, 2H),
3.07 (d, 2H). HRMS: calcd for C28H26ClN5O3 þ Hþ, 516.17969; found
(ESI-FTMS, [M þ H]1þ), 516.1806.
1H NMR (400 MHz, DMSO-d6)
d 9.47 (s, 1H), 9.18 (d, 1H), 8.37 (m,
2H), 8.17 (m, 2H), 7.51 (s, 1H), 7.36 (bs, 2H), 7.31 (m, 2H), 7.12 (m,
2H), 4.08 (s, 3H), 3.99 (m, 2H), 3.97 (s, 3H), 2.89 (m, 1H), 2.65 (m,
1H). HRMS: calcd for C28H26FN5O3 þ Hþ, 500.20924; found (ESI-
FTMS, [M þ H]1þ), 500.20938.
5.3.38. 2-(5-{[(2S)-2-Amino-3-pyridin-4-ylpropyl]oxy}pyridin-3-
yl)-8,9- dimethoxybenzo[c]-2,7-naphthyridin-4-amine (9s)
5.3.31. 2-(5-{[(2R)-2-Amino-3-(4-
1H NMR (400 MHz, DMSO-d6)
d 9.64 (s, 1H), 9.26 (s, 1H), 8.72 (d,
fluorophenyl)propyl]oxy}pyridin-3-yl)-8,9- dimethoxybenzo[c]-2,7-
naphthyridin-4-amine*HCl (9k)
2H), 8.49 (d, 1H), 8.43 (s, 1H), 8.38 (bs, 2H), 8.25 (s, 1H), 8.18 (s, 1H),
7.68 (d, 2H), 7.59 (s, 1H), 4.38 (m, 1H), 4.21 (m, 1H), 4.11 (s, 3H),
4.08 (m, 3H), 4.01 (s, 3H), 3.22 (d, 2H). HRMS: calcd for
C27H26N6O3 þ Hþ, 483.21391; found (ESI-FTMS, [M þ H]1þ),
483.21474.
1H NMR (400 MHz, DMSO-d6)
d 9.52 (s, 1H), 9.25 (d, 1H), 8.44
(m, 2H), 8.38 (s, 1H), 8.24 (bs, 2H), 8.18 (m, 1H), 7.53 (s, 1H), 7.44
(bs, 1H), 7.38 (m, 2H), 7.20 (m, 2H), 4.31 (m, 1H), 4.13 (m, 1H), 4.08
(s, 3H), 3.98 (s, 3H), 3.06 (d, 2H). HRMS: calcd for
C28H26FN5O3 þ Hþ, 500.20924; found (ESI-FTMS, [M þ H]1þ),
500.20747.
Acknowledgments
The authors wish to thank Drs. Tarek Mansour and Robert
Abraham for their support and encouragement provided during the
course of this work. We also would like to thank the members of
the Wyeth Chemical Technologies group for analytical and spectral
determinations.
5.3.32. 2-[5-({(2S)-2-Amino-3-[3-
(trifluoromethyl)phenyl]propyl}oxy)pyridin-3-yl]-8,9-
dimethoxybenzo[c]-2,7-naphthyridin-4-amine (9l)
1H NMR (400 MHz, CDCl3)
d 9.21 (s, 1H), 8.96 (s, 1H), 8.40 (s,
1H), 8.01 (s, 2H), 7.78 (s, 1H), 7.58 (s, 1H), 7.53 (m, 2H), 7.46
(m, 2H), 5.49 (bs, 2H), 4.17 (s, 3H), 4.10 (s, 3H), 4.03 (m, 2H), 3.56
(m, 1H), 3.08 (m, 1H), 2.83 (m, 1H). HRMS: calcd for
C29H26F3N5O3 þ Hþ, 550.20605; found (ESI-FTMS, [M þ H]1þ),
550.20615.
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2H), 4.08 (s, 3H), 3.98 (s, 3H), 3.70 (m,1H), 3.18 (m,1H), 3.02 (m,1H).