An
NH4Cl-catalyzed ethoxy ethyl deprotection was developed
for the synthesis of merestinib, a MET inhibitor. Alternative reactor
technologies using temperatures above the solvent boiling point are
combined with this mild catalyst to promote the deprotection reaction.
The reaction is optimized for flow and has been used to synthesize
over 100 kg of the target compound. The generality of the reaction
conditions is also demonstrated with other compounds and protecting
groups.
A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acyclic intermediates underwent base-catalyzed rearrangement involving C-C and N-N bond formation followed by ring expansion and yielded resin-bound dihydroquinazoline-2-carboxylic acids. After they were released from the resin by treatment with trifluoroacetic acid, base-mediated decarboxylation produced the target quinazolines in moderate-to-high yields and purities.
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