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<example id="h0131" title="EXAMPLE 58"><heading id="h0132" title="N-(3,5-dichlorobenzyl)-8-hydroxy-5-(4-methylpiperazin-1-yl)-1,6-naphthyridine-7-carboxamide"><p id="p0257" num="0257">
<chemistry id="chem0134" num="0134"><img id="ib0134" file="imgb0134.tif" wi="67" he="52" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0258" num="0258">To a solution of 5-bromo-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide from Example 50 (25 mg, 0.060 mmol), N-methyl piperazine (35.2 mg, 0.35 mmol) in DMF (0.25 ml) was heated at 135C for 48 hrs. The reaction mixture was diluted with DMF (0.25 ml) and purified by preparative HPLC. (Gilson semi preparative HPLC system and a YMC Combiprep Pro Column (50X20mm LD., 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>13.0</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>9.21</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>4.2</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.36</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>8.4</point></value> and <value><point>1.5</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.25</point></value></quantity> (1, <quantity type="peaktype">t</quantity>, J=<quantity type="coupling"><value><point>6.4</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.65</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>4.2</point></value> and <value><point>8.4</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>3</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>4.67</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>, <peak><quantity type="shift"><value><point>3.79</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>11.9</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>3.60</point></value></quantity> (<quantity type="integral"><value><point>4</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>3.19</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak> and <peak><quantity type="shift"><value><point>2.96</point></value></quantity> (<quantity type="integral"><value><point>3</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak> ppm</peaks></spectrum>.<br/>
FAB MS calcd for C<sub>21</sub>H<sub>21</sub>Cl<sub>2</sub>N<sub>5</sub>O<sub>3</sub> 446 (MH<sup>+</sup>), found 446.<br/>
FAB HRMS exact mass calc'd for C<sub>21</sub>H<sub>21</sub>Cl<sub>2</sub>N<sub>5</sub>O<sub>3</sub> 446.1145 (MH<sup>+</sup>), found 446.1138.</p></heading></example>
