An alternative synthesis of Vandetanib (CaprelsaTM) via a microwave accelerated Dimroth rearrangement

Description

Yes / Vandetanib is an orally available tyrosine kinase inhibitor used in the treatment of cancer. The current
synthesis proceeds via an unstable 4-chloroquinazoline, using harsh reagents, in addition to requiring
sequential protection and deprotection steps. In the present work, use of the Dimroth rearrangement
in the key quinazoline forming step enabled the synthesis of Vandetanib in nine steps (compared to
the previously reported 12–14). / This work was supported by the Cancer Research UK-Cancer Imaging Centre (grant: C1060/ A16464), the Institute of Cancer Research and the University of Hull.

Links & Downloads

1. Brocklesby KL, Waby JS, Cawthorne C et al (2017) An alternative synthesis of Vandetanib (CaprelsaTM) via a microwave accelerated Dimroth rearrangement. Tetrahedron Letters. 58(15): 1467-1469.
2. http://hdl.handle.net/10454/17298
3. https://doi.org/10.1016/j.tetlet.2017.02.082

Tags

Vandetanib

Quinazoline

Dimroth rearrangement

Tyrosine kinase inhibitor

Additional Fields

Identifer	oai:union.ndltd.org:BRADFORD/oai:bradscholars.brad.ac.uk:10454/17298
Date	10 October 2019
Creators	Brocklesby, K.L., Waby, Jennifer S., Cawthorne, C., Smith, G.
Source Sets	Bradford Scholars
Language	English
Detected Language	English
Type	Article, Published version
Rights	©2017 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license (http:// creativecommons.org/licenses/by/4.0/).