N-nitroso ticagrelor

During the N-Nitroso Ticagrelor synthesis, we encountered that no N-Nitrosation actually took place, and rather formation of some other NO-aduct (having the same Mass) has been isolated.
However, there are several companies that offers N-Nitroso Ticagrelor and what a surprise, N-Nitroso Ticagrelor have already its own CAS no. 2476859-55-7.
How exiting was, when I today came across online available document from MSN labs, where the MSN team experienced exactly the same issue; and describes proposed mechanism of Ticagrelor nitrosation, including cyclopropyl ring-opening, C-nitrosation followed by cyclization leading to 4,5-Dihydroisoxasole Derivate:
Have you experienced the same?


We are working on synthesis of some ticagrelor nitrosamines derivatives…
will share our experience soon. thanks for the update

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Interesting mechanism!

If synthesis proves impossible, this falls into the same bucket as the dipines - nitrosamines that would theoretically be category 5 but in practice do not form thus are not a concern at all. Anecdotally, something similar to your experience with contract manfacturers has also occured - a product is available claiming to provide nitroso-amlodipine, but upon delivery the compound proved to be something else…

See the current thread on the dipines for more discussion.


dipines do not form nitroso on the piperidine nitrogen , under nitrosation conditions they aromatize to form corresponding pyridine analogs… this is our practical experience…