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<example id="h0153" title="EXAMPLE 69"><heading id="h0154" title="8-Hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide"><p id="p0279" num="0279">
<chemistry id="chem0145" num="0145"><img id="ib0145" file="imgb0145.tif" wi="75" he="43" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0280" num="0280">To a 5 mL pyrex pressure vessel with a stirring bar was added 5-bromo-8-hydroxy-[1,6]naphthyridine-7-carboxylic acid 3,5-dichloro-benzylamide (0.055g, 0.13 mmol), thiophenol (0.056g, 0.50 mmol) and triethylamine (0.28 mL, 2.00 mmol). The vessel was sealed under nitrogen and the stirred mixture heated in a 135°C oil bath for 24h. The cooled reaction mixture was concentrated <i>in vacuo</i> and the residue was chromatographed on silica gel (15g) using methanol:chloroform (5:95) as eluant to give 8-hydroxy-5-phenylsulfanyl-[1,6]naphthyridine-7-carboxylic acid 3,5-dichlorobenzylamide as a solid.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">CDCl3</quantity>, <quantity type="frequency"><value><point>300</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>12.53</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>9.20</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>5</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>8.58</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>2</point></value>,<value><point>8</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.66</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>5</point></value>, <value><point>8</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.50</point></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>7.30</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>7.08</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>4.40</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</point></value><units>Hz</units></quantity>)</peak></peaks></spectrum>.<br/>
FAB MS calc'd for C<sub>22</sub>H<sub>15</sub>Cl<sub>2</sub>N<sub>3</sub>O<sub>2</sub>S 456 (MH<sup>+</sup>), found 456.</p></heading></example>
