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<example id="h0129" title="EXAMPLE 57"><heading id="h0130" title="N-(3,5-dichlorobenzyl)-8-hydroxy-5-phenoxy-1,6-naphthyridine-7-carboxamide"><p id="p0255" num="0255">
<chemistry id="chem0133" num="0133"><img id="ib0133" file="imgb0133.tif" wi="62" he="59" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0256" num="0256">To a solution of 5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 50 (26 mg, 0.068 mmol), phenol (28mg, 0.304 mmol) and cesium carbonate (198 mg, 0.608 mmol) in DMPU (0.25 ml) was heated at 140C for 8 hrs. The reaction was poured into sat aq. Na<sub>2</sub>CO<sub>3</sub> and extracted with CHCl<sub>3</sub>. The organic phase was washed with water and dried (Na<sub>2</sub>SO<sub>4</sub>). The solvent was evaporated <i>in vacuo</i> and the residue dissolved in DMF (0.7ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50X20mm I.D., C18, S-5 um, 120A) eluting with 5 - 95% acetonitrile/water (0.1% TFA) at 15 ml/min) to afford the title compound after lyophilization.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">CDCl3</quantity>, <quantity type="frequency"><value><point>400</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>12.55</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>9.31</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>4.4</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.80</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>8.4</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.78</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">dd</quantity>, J=<quantity type="coupling"><value><point>4.4</point></value> and <value><point>8.4</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.61</point></value></quantity>(<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">t</quantity>, J=<quantity type="coupling"><value><point>5.5</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.44</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">t</quantity>, J=<quantity type="coupling"><value><point>7.9</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><min>7.35</min>-<max>7.20</max></value></quantity> (<quantity type="integral"><value><point>6</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.10</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>1.8</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>4.49</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, J=<quantity type="coupling"><value><point>6.2</point></value> <units>Hz</units></quantity>)</peak> ppm</peaks></spectrum>.<br/>
FAB MS calcd for C<sub>22</sub>H<sub>15</sub> Cl<sub>2</sub>N<sub>3</sub>O<sub>3</sub> 440 (MH<sup>+</sup>), found 440.</p></heading></example>
