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Synthesis of m-chloro anilide complete compound #152

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tscmacdonald opened this Issue Feb 11, 2014 · 3 comments

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complete amide scheme m-chloroaniline

A complete scheme for synthesis of a Series 4 product (issue #122 ). If this all works well, it should provide a repeatable route for different amides in future.

Hydrazone formation and subsequent cyclisation conditions have been taken from DOI: 10.1002/anie.201001999, with 90% and 75% yields reported for the coupling and cyclisation steps respectively of this similar compound:

thielheterocycle

Amide coupling has been successfully performed as of 10/2/14, yield 83 %: http://malaria.ourexperiment.org/triazolopyrazine_se/8995/Preparation_of_6chloroN3chlorophenylpyrazine2carboxamide_with_T3P_TM_12.html

(pyridine was used as a base here, but DIPEA will be used in future)

An update to this: synthesis possibly finished (need to run some more tests), albeit without a particualrly impressive yield.

Working backwards from the most recent chemistry:
Oxidative cyclisation

Hydrazone-forming condensation

Synthesis of hydrazine

Synthesis of anilide

Overall yield seems to be about 40 mgs of final product (if it was successfully formed: this has yet to be shown as of 6/3/14) from 200 mgs of amide.

Edit: ignore me closing and reopening this issue; I am bad at github.

@tscmacdonald tscmacdonald reopened this Mar 6, 2014

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mattodd commented Jun 29, 2014

OSM-S-202
Done?

Owner

mattodd commented Dec 10, 2014

Compound made and evaluated.

http://malaria.ourexperiment.org/biological_data/10456/IC50_determination_of_Compounds_Sent_to_GSK.html

Link about alternative synthetic route (timing of hydrazone formation) added to Series 4 wiki.

Closing.

@mattodd mattodd closed this Dec 10, 2014

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