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Synthesis of m-chloro anilide complete compound #152

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:


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


mattodd commented Jun 29, 2014



mattodd commented Dec 10, 2014

Compound made and evaluated.


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


@mattodd mattodd closed this Dec 10, 2014

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