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<example id="h0280" title="EXAMPLE 123"><heading id="h0281" title="N-(2,3-dimethoxybenzyl)-5-{[4-(dimethylamino)phenyl]thio}-8-hydroxy-1,6-naphthyridine-7-carboxamide"><p id="p0400" num="0400">
<chemistry id="chem0199" num="0199"><img id="ib0199" file="imgb0199.tif" wi="105" he="65" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0401" num="0401">Into a pressure reactor was placed 5-bromo-N-(2,3-dimethoxybenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (.1 g, .24 mmol), 4-(dimethylamino)-benzenethiol (.147 g, .96 mmol) and triethylamine (.363 g, .5 mL, 3.59 mmol). The vessel was purged with nitrogen gas, sealed and heated to 135 °C for 18 hours, after which time it was cooled and the excess triethylamine removed <i>in vacuo.</i> The residue was partitioned between EtOAc/water and extracted. The combined organic extracts were washed with brine, dried over Na<sub>2</sub>SO<sub>4</sub>, filtered and the solvent removed. The resulting glass was triturated with diethyl ether and filtered to yield N-(2,3-dimethoxybenzyl)-5-{[4-(dimethylamino)phenyl]thio}-8-hydroxy-1,6-naphthyridine-7-carboxamide as a solid.<br/>
<sup>1</sup>H NMR (CDCl<sub>3</sub>, 400MHz) δ□9.16 (1H, dd, <i>J</i>=1.6Hz), 4.3Hz); 8.61 (1H, dd, <i>J</i>=1.5Hz, 8.4Hz); 7.80 (1H, m); 7.63 (1H, dd, <i>J</i>=4.3Hz, 8.4Hz); 7.40 (2H, d, <i>J</i>=8.9 Hz); 7.02 (1H, t, <i>J</i>=8.0Hz); 6.87 (1H, d, <i>J</i>=7.1Hz); 6.77 (1H, d, <i>J</i>=7.7Hz); 6.63 (2H, d, <i>J</i>=8.9Hz); 4.56 (2H, d, <i>J</i>=6.3Hz); 3.88 (3H, s); 3.80 (3H, s); 2.89 (6H, s)<br/>
FAB MS calcd for C<sub>26</sub>H<sub>26</sub>N<sub>4</sub>O<sub>4</sub>S 491 (MH<sup>+</sup>), found 491.</p></heading></example>
