Timcodar dimesilate, VX-853

Chemical Name: N1-Benzyl-4-chloro-N2-methyl-N2-[2-oxo-2-(3,4,5-trimethoxyphenyl)acetyl]-N1-[3-(4-pyridyl)-1-[2-(4-pyridyl)ethyl]propyl]-L-phenylalaninamide dimethanesulfonate
CAS No. 183313-30-6, 179033-51-3 (free base)
项目整合开发状态: Phase I/II
项目研究机构: Vertex (Originator)
合成路线:Condensation of 1,3-acetonedicarboxylic acid (I) with pyridine-4-carboxaldehyde (II) and subsequent acid decarboxylation produced 1,5-dipyridylpentadienone (III),which was reduced to the saturated ketone (IV) by transfer hydrogenation using formic acid and Pd/C.Condensation of (IV) with benzyl amine (V) in benzene with azeotropical removal of water,followed by reduction of the intermediate imine with NaBH4 gave rise to the secondary amine (VI).Coupling of (VI) with N-Boc-N-methyl-L-4-chlorophenylalanine (VII) in the presence of EDC afforded amide (VIII).After Boc deprotection of (VIII) with trifluoroacetic acid,the resulting amine (IX) was coupled with 3,4,5-trimethoxybenzoylformic acid (X) to furnish the title compound.