Proposed Synthesis of 'compound 3' and 'compound 4'

06 Feb
Published by JimCronshaw

The following compounds have been identified as potential antimalarial drugs by GSK-Tres Cantos.
Target Molecules
The top compound, known hereafter as 'compound 3', can be found on ChEMBL and ChemSpider:
https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL535225 - ChEMBL
https://www.chemspider.com/Chemical-Structure.15995932.html?rid=1e70c7d6... - ChemSpider
 
As can the bottom compound, known hereafter as 'compound 4':
https://www.ebi.ac.uk/chembldb/index.php/compound/inspect/CHEMBL581088 - ChEMBL
https://www.chemspider.com/Chemical-Structure.24575349.html?rid=a5689148... - ChemSpider
 
My first job as a new honours student in the Todd group will be to re-synthesise these compounds. A synthesis strategy for each compound is shown below, beggining with 'compound 3'
 

Step 3, involving chlorine gas, is problematic. Any suggestions on how to get around this step would be greatly appreciated, as would any general feedback on how to improve this synthesis. The literature for this synthesis will shortly be uploaded to Mendeley in the OSDDMalaria group.
 
A synthesis strategy for 'compound 4' is shown below:

Again, any feedback on this synthesis will be greatly appreciated. The relevant literature will shortly be available on Mendeley in the OSDDMalaria group as well.
 
Apologies for the formatting of the two synthesis strategies. I wasn't able to activate my Chemdraw software over the internet so I had to activate it over email, and so I'm using ChemSketch until they send me an activation code.
 
Further detail on the availability of reagents is available in my lab book, found here: http://openwetware.org/wiki/User:Jim_Cronshaw/Notebook/OSDDMalaria:GSKTr...