<?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="h0179" title="EXAMPLE 80"><heading id="h0180" title="1-(7-{[(3,5-dichlorobenzyl)amino]carbonyl}-8-hydroxy-1,6-naphthyridin-5-yl)-4-(2-oxo-2-pyrrolidin-1-ylethyl)piperazine"><p id="p0304" num="0304">
<chemistry id="chem0156" num="0156"><img id="ib0156" file="imgb0156.tif" wi="74" he="72" img-content="chem" img-format="tif" orientation="portrait" inline="no"/></chemistry></p><p id="p0305" num="0305">The title compound was prepared as the piperazin-4-ium trifluoroacetate salt using the procedure described in Example 58 replacing N-methylpiperazine with 1-(2-oxo-2-pyrrolidin-1-ylethyl)piperazine.<br/>
<spectrum type="hnmr">1H NMR (<quantity type="solvent">CD3OD</quantity>, <quantity type="frequency"><value><point>400</point></value><units>MHz</units></quantity>) δ <peaks type=".."><peak><quantity type="shift"><value><point>9.10</point></value></quantity> (<quantity type="integral"><value><point>1</point></value><units>H</units></quantity>, <quantity type="peaktype">d</quantity>, <quantity type="comment">4.3Hz</quantity>)</peak>, <peak><quantity type="shift"><value><point>8.64</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>8.6</point></value><units>Hz</units></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>4.3</point></value> and <value><point>8.6</point></value><units>Hz</units></quantity>)</peak>, <peak><quantity type="shift"><value><point>7.37</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>7.36</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>4.65</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>4.27</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">s</quantity>)</peak>, <peak><quantity type="shift"><value><point>3.51</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><min>3.42</min>-<max>3.96</max></value></quantity> (<quantity type="integral"><value><point>8</point></value><units>H</units></quantity>, <quantity type="peaktype">br m</quantity>)</peak>, <peak><quantity type="shift"><value><point>2.05</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>1.94</point></value></quantity> (<quantity type="integral"><value><point>2</point></value><units>H</units></quantity>, <quantity type="peaktype">m</quantity>)</peak>ppm</peaks></spectrum>.<br/>
FAB MS calcd for C<sub>26</sub>H<sub>28</sub>Cl<sub>2</sub>N<sub>6</sub>O<sub>3</sub> 543.2 (MH<sup>+</sup>), found 543.1.<br/>
FAB HRMS exact mass calcd for C<sub>26</sub>H<sub>28</sub>Cl<sub>2</sub>N<sub>6</sub>O<sub>3</sub> 543.1673 (MH<sup>+</sup>), found 543.1678.</p></heading></example>
