890086-36-9

Upstream product

• 117523-91-8 N-[4-(hydroxymethyl)-3-methylphenyl]acetamide 
• 75-36-5 acetyl chloride 
• 63405-88-9 4-amino-2-methyl-benzyl alcohol 
• 99-51-4 4-nitro-o-xylene 

Downstream Products

• 838858-88-1 4-(acetylamino)-5-bromo-2-methylbenzyl acetate 
• 838858-87-0 N-[4-(acetyloxymethyl)-2-cyano-5-methylphenyl]-acetamide 

Relevant academic research and scientific papers

Chemical development of ZD9331: Synthesis of a bromomethylquinazolinone avoiding a nonselective radical bromination

An efficient regiospecific synthesis of ZD9331 Pivaloyloxymethyl (POM) Bromide (4) has been accomplished via ZD9331 Quinacetate HCl (15) avoiding a nonselective bromination. The original route used a radical bromination on a substrate with three methyl groups, which generated a range of bromomethyl derived compounds that carried through to the final active pharmaceutical ingredient (API). A strategy, based on the Zinin reaction, was developed to synthesize the required bromomethyl compound in a regioselective manner. This approach was successfully scaled to manufacture a tonne of material.

SYNTHETIC METHOD

A quinazolin-4-one derivative of formula (I), may be made by a process including the step of cyclization an amide of formula (II), to form a quinazolin-4-one derivative of formula (III).