<?xml version="1.0" encoding="UTF-8"?>
<!--

       Copyright 2011 Peter Murray-Rust et. al.

       Licensed under the Apache License, Version 2.0 (the "License");
       you may not use this file except in compliance with the License.
       You may obtain a copy of the License at

           http://www.apache.org/licenses/LICENSE-2.0

       Unless required by applicable law or agreed to in writing, software
       distributed under the License is distributed on an "AS IS" BASIS,
       WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
       See the License for the specific language governing permissions and
       limitations under the License.

-->

<example id="h0244" title="EXAMPLE 111"><heading id="h0245" title="N-(3,5-difluorobenzyl)-8-hydroxy-5-(methylsulfonyl)-1,6-naphthyridine-7-carboxamide"><p id="p0368" num="0368">
<chemistry id="chem0187" num="0187"><img id="ib0187" file="imgb0187.tif" wi="74" he="40" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0369" num="0369">Into a round bottom flask fitted with a nitrogen inlet, condenser and a magnetic stirring bar was placed 5-bromo-N-(3,5-difluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide (.1 g, .25 mmol), sodium methanesulfinate (.061 g, .6 mmol) and 2 mL DMF. The mixture was heated to 100 °C for 48 hours, after which time the reaction was cooled, poured into water and extracted with CH<sub>2</sub>Cl<sub>2</sub>. The combined organic extracts were washed with brine, dried over Na<sub>2</sub>SO<sub>4</sub>, filtered and the solvent removed <i>in vacuo.</i> The resulting crude product was purified by reverse phase HPLC to obtain N-(3,5-difluorobenzyl)-8-hydroxy-5-(methylsulfonyl)-1,6-naphthyridine-7-carboxamide trifluoroacetate salt as a yellow crystalline solid.<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>9.34</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>8.7</point></value><units>Hz</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>9.29</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>4.1</point></value><units>Hz</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>8.17</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>7.80</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><units>Hz</units></quantity>, <quantity type="comment">8.8Hz</quantity>)</peak>; <peak><quantity type="shift"><value><point>6.92</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>5.8</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>6.77</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>8.8</point></value><units>Hz</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>4.72</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>6.5</point></value><units>Hz</units></quantity>)</peak>; <peak><quantity type="shift"><value><point>3.38</point></value></quantity> (<quantity type="integral"><value><point>3</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak></peaks></spectrum><br/>
FAB HRMS exact mass calcd for C<sub>17</sub>H<sub>13</sub> F<sub>2</sub> N<sub>3</sub>O<sub>4</sub>S 394.0668 (MH<sup>+</sup>), found 394.0675.</p></heading></example>
