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<example id="h0312" title="EXAMPLE 135"><heading id="h0313" title="5-[[2-(Dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide"><p id="p0431" num="0431">
<chemistry id="chem0211" num="0211"><img id="ib0211" file="imgb0211.tif" wi="76" he="53" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0432" num="0432">Into a 10 mL pressure vessel equipped with a magnetic stir bar was placed 0.1 g (.266 mmol) 5-bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (see Example 126), 0.031 g (.27 mmol) N,N-dimethyl-2-(methylamino)acetamide, .726 mL (.8 mmol) N,N-diisopropylethylamine and 5 mL DMF. The vessel was sealed and heated on an oil bath to 135°C for 18 hrs., after which the mixture was cooled and the solvent removed <i>in vacuo</i>. The residue was purified by reverse phase HPLC on a C<sub>18</sub> column using acetonitrile/water as eluent to give 5-[[2-(dimethylamino)-2-oxoethyl](methyl)amino]-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="frequency"><value><point>300</point></value> <units>MHz</units></quantity>, <quantity type="solvent">CDCl3</quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>9.22</point></value></quantity> (<quantity type="peaktype">dd</quantity>, J = <quantity type="coupling"><value><point>1.4</point></value><units>Hz</units></quantity>, J = 4.4Hz, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>8.57</point></value></quantity> (<quantity type="peaktype">dd</quantity>, J = <quantity type="coupling"><value><point>1.4</point></value><units>Hz</units></quantity>, J = 8.6Hz, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>8.37</point></value></quantity> (<quantity type="peaktype">t</quantity>, J = <quantity type="coupling"><value><point>4.5</point></value><units>Hz</units></quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>7.65</point></value></quantity> (<quantity type="peaktype">dd</quantity>, J = <quantity type="coupling"><value><point>4.4</point></value><units>Hz</units></quantity>, J = 8.5Hz, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>7.41</point></value></quantity> (<quantity type="peaktype">d</quantity>, J = <quantity type="coupling"><value><point>8.3</point></value><units>Hz</units></quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>7.40</point></value></quantity> (<quantity type="peaktype">d</quantity>, J = <quantity type="coupling"><value><point>8.3</point></value><units>Hz</units></quantity>, <quantity type="integral"><value><point>1</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>7.06</point></value></quantity> (<quantity type="peaktype">t</quantity>, J = <quantity type="coupling"><value><point>8.5</point></value><units>Hz</units></quantity>, <quantity type="integral"><value><point>2</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>4.65</point></value></quantity> (<quantity type="peaktype">d</quantity>, J = <quantity type="coupling"><value><point>6.1</point></value><units>Hz</units></quantity>, <quantity type="integral"><value><point>2</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>4.08</point></value></quantity> (<quantity type="peaktype">s</quantity>, <quantity type="integral"><value><point>2</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>3.15</point></value></quantity> (<quantity type="peaktype">s</quantity>, <quantity type="integral"><value><point>3</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>2.99</point></value></quantity> (<quantity type="peaktype">s</quantity>,<quantity type="integral"><value><point>3</point></value><units>H</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>2.80</point></value></quantity> (<quantity type="peaktype">s</quantity>, <quantity type="integral"><value><point>3</point></value><units>H</units></quantity>)</peak></peaks></spectrum><br/>
HRMS calc for C<sub>21</sub>H<sub>22</sub>FN<sub>5</sub>O<sub>3</sub> (M+1): calc, 412.1766; found, 412.1779</p></heading></example>
