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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 3
BKCSDE 32(3)
March 20, 2011 

An Improved Convergent Approach for Synthesis of Erlotinib, a Tyrosine Kinase Inhibitor, via a Ring Closure Reaction of Phenyl Benzamidine Intermediate
Davoud Asgari*, Ayuob Aghanejad, Javid Shahbazi Mojarrad
Erlotinib, Phenyl benzamidine, EGFR-tyrosine kinase, Non-small-cell lung cancer, Dimroth rearrangement
An improved convergent and economical method has been developed for the synthesis of erlotinib, a 4-anilinoquinazoline and an EGFR-tyrosine kinase inhibitor for treatment of non-small-cell lung cancer. The final two steps for the formation of this 4-anilinoquinazoline from suitable 2-aminobenzonitrile intermediate and 3-ethynylaniline were modified and were performed in a simple one-pot reaction. The ring-closing mechanism for the formation of erlotinib from the suitable formamidine intermediate and 3-ethynylaniline was investigated and determined to proceed via the formation of phenyl benzamidine intermediate rather than involving Dimroth rearrangement reported earlier. The new benzamidine intermediate was isolated for the first time and characterized.
909 - 914
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