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19th February 2014 @ 06:22



There is progress towards some of the final analogues for testing in Series 3. Over the summer project, compounds 3, 4, 5, 6 and 7 were synthesised for coupling to produce the analogs 8 and 9. The reaction conditions for 7 were optimised and ensured consistency of yield. Progress is being made towards the synthesis of 5 then 6 to couple with 7 to produce the analog 10. At the moment, 6 has been synthesised and requires purification.

The final coupling of 8, 9 and hopefully 10 will take place by the end of this week, along with their purification if possible.  

Update 21/02/2013: The coupling of 8 was unsuccessful, and no other couplings were attempted by the end of the summer scholarship. Compound 6 will be used as crude due to difficulties with purification.

Future synthesis work to wrap up Series 3: 

1. (Re)Attempt the Suzuki coupling reaction to produce the analogs 8, 9 and 10 + purification for characterisation and biological testing

2. Synthesise analogs of the thienopyrimidine half (7) with methylamine, ethanolamine and N,N-dimethylethylenediamine (or N-methylethylenediamine) instead of ammonia substitution (should be able to do without the pressure tubes). These can then be coupled with the boronic ester of the (unsubstituted) benzenesulfonamide. 

3. Synthesise analogs of the boronic ester by substituting pyrrolidine or ethanolamine onto the sulfonyl chloride, and subsequent conversion to the boronic ester. These can then be coupled with the thienopyrimidine (7). 

Other work:

4. Check that all synthesised compounds have been assigned an OSM number, and whether there is still a sample of the compound

5. Check literature for whether the OSM compounds have been previously synthesised and/or characterised

6. Check whether enough characterisation data has been collected for each compound. If not enough and there is no remaining sample, then it will need to be resynthesised. 

7. Write up experimental procedure for the compounds

Attached Files
14th January 2014 @ 22:26

Hi there! I'm Carmen, an undergraduate student starting work on the OSM project, and will be taking this chance to introduce myself and some of my work. 

I've just finished my second year of B. Sc. (Adv) at the University of Sydney, and will be spending six weeks of my summer break working with Dr Mat Todd and Dr Alice Williamson on a USYD School of Chemistry Summer Scholarship. Currently, my project is to help wrap up Series 3 by synthesising some of the last proposed compounds for testing and assisting with collating the data for the whole series. 

What drew me to the OSM project was both its medical relevance in tackling a major infectious disease, and its unique open source format driving towards that goal. It's an exciting opportunity for both learning about synthetic medicinal chemistry and engaging with the open source structure, where everything I do is accessible for anyone to view or join in. I've done short projects with other research groups, but this is definitely a completely new experience to me, and will likely lead to some better habits and record keeping on my end! 

My past couple of days can be summed up as getting familiar with the lab, learning about the different platforms for communication in the project (and acquiring a whole new bundle of accounts) and writing up proper ELN entries, and of course, some chemistry on the side. 

Anyway, that's enough from me for now. Looking forward to working with everyone! 

Carmen Tran (CT)