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<example id="h0159" title="EXAMPLE 72"><heading id="h0160" title="5-(3-aminopyrrolidin-1-yl)-N-(3,5-dichlorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide"><p id="p0285" num="0285">
<chemistry id="chem0148" num="0148"><img id="ib0148" file="imgb0148.tif" wi="72" he="52" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0286" num="0286">A solution of the derivative prepared in Example 71 (10mg, 0.0188 mmol) in CH<sub>2</sub> Cl<sub>2</sub> (2 ml) was treated with trifluroacetic acid (TFA) (0.5 ml) and stirred at room temperature for 1 hr. The solvent was evaporated in vacuo and the residue 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 trifluoroacetate salt of the title compound after lyophilization.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">DMSO-d6</quantity>, <quantity type="frequency"><value><point>400</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>12.61</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>9.32</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>6.6</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>9.09</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>1.5</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.68</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>8.6</point></value> and <value><point>1.5</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.04</point></value></quantity> (<quantity type="integral"><value><point>3</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>8.21</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>6.0</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.75</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>8.6</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.53</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>1.9</point></value> <units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.41</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>1.9</point></value> <units>Hz</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>4.58</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>6.4</point></value><units>Hz</units></quantity>)</peak> <peak><quantity type="shift"><value><min>4.10</min>-<max>3.90</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><min>3.85</min>-<max>3.60</max></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>2.32</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>, <peak><quantity type="shift"><value><point>2.08</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak> ppm</peaks></spectrum>.<br/>
FAB MS calcd for C<sub>20</sub>H<sub>19</sub>Cl<sub>2</sub>N<sub>5</sub>O<sub>2</sub> 432 (MH<sup>+</sup>), found 432.<br/>
FAB HRMS exact mass calc'd for C<sub>20</sub>H<sub>19</sub>Cl<sub>2</sub>N<sub>5</sub>O<sub>2</sub> 432.0989 (MH<sup>+</sup>), found 432.0994.</p></heading></example>
