Synthesis of 6-chloropyrazine-2-carboxylic acid #150

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IngaTopolnicki opened this Issue Feb 5, 2014 · 3 comments

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Being able to synthesise this molecule in bulk is important because it is a precursor in the synthesis of the triazolopyrazine core for series four amides (see http://malaria.ourexperiment.org/the_osm_blog/8173/post.html for amide synthetic plan).
I’m following the method used by Eduvie Omene:
synthesis of 6-chloropyrazine-2-carboxylic acid
Are these procedures from the literature Eduvie? I found a paper using your method for the synthesis of OSM-S-148 and OSM-S-149 (DOI: 10.1021/jm201045m, see p. 7688).
The ELN entries for this synthesis can be found here:
http://malaria.ourexperiment.org/triazolopyrazine_se/8634/Synthesis_of_methyl_pyrazine2carboxylate_IT_11.html
http://malaria.ourexperiment.org/triazolopyrazine_se/8938/Synthesis_of_methyl_4oxy2pyrazine_carboxylate_IT_21.html
http://malaria.ourexperiment.org/triazolopyrazine_se/9027/Synthesis_of_methyl_6chloro2pyrazinecarboxylate_IT_31.html
http://malaria.ourexperiment.org/triazolopyrazine_se/9147/Synthesis_of_6chloropyrazine2carboxylic_acid_IT_41.html

Hopefully this will be finished in two weeks time.

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alintheopen commented Feb 5, 2014

Nice post Inga - Eduvie (@PatrickThomson), if you have followed literature procedures please pop in the references to your ELN entries. We also need to discuss OSM-E numbers.

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mattodd commented Feb 19, 2014

OK, so if your melting point is OK and your NMR is fine, are we able to close this Issue, @IngaTopolnicki ?

The melting point wasn’t as great as I’d hoped 151.7 - 153.3 °C compared to commercial m.p. 154.8 - 158.2 °C. But I’ll still close the issue because the NMR looks good and I think the product is still pure enough to be used for further reactions.

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