Imatinib → 4-(Chloromethyl)-N-(4-methyl-3-((4-(3-pyridinyl)-2-pyrimidinyl)amino)phenyl)benzamide

Participants

Reaction Steps

Scheme 3 illustrates a third synthetic pathway for preparation of imatinib base, referred to herein as “Method C.” This method is described in WO 2004/108699 and in J. Med. Chem. 2005, 48(1), 249-255, and comprises the condensation of 4-methyl-N-3-(4-pyridin-3-yl-pyrimidin-2-yl)benzene-1,3-diamine with 4-chloromethylbenzoyl chloride to yield 4-chloromethyl-N-(4-methyl-3-((4-pyridin-3-yl)-pyrimidin-2-ylamino)-phenyl)-benzamide, followed by the reaction of 4-chloromethyl-N-(4-methyl-3-((4-pyridin-3-yl)-pyrimidin-2-ylamino)-phenyl)-benzamide with N-methylpiperazine.

Provenance & Evidence