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Synthesis of Isotope-Labeled HSP90 Inhibitor: [(13) CD3 ] and [(14) C]-TAK-459

Synthesis of Isotope-Labeled HSP90 Inhibitor: [(13) CD3 ] and [(14) C]-TAK-459

Mihaela Plesescu, Eric L Elliott, Yuexian Li, Shimoga R Prakash

J Labelled Comp Radiopharm. 2014 Jul;57(9):574-8.

PMID: 24992204

Abstract:

[(13) CD3 ]-TAK-459 (1A), an HSP90 inhibitor, was synthesized from [(13) CD3 ]-sodium methoxide in three steps in an overall yield of 29%. The key intermediate [(13) CD3 ]-2-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine was synthesized in two steps from 2,6-dibromopyridine and stable isotope-labeled sodium methoxide. [(14) C]-TAK-459 (1B) was synthesized from [(14) C(U)]-guanidine hydrochloride in five steps in an overall radiochemical yield of 5.4%. The key intermediate, [(14) C]-(R)-2-amino-7-(2-bromo-4-fluorophenyl)-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5(6H)-one, was prepared by microwave-assisted condensation.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP1247726857	6-Bromo-2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine		1247726-85-7	Price
LS793282	2-Chloro-5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine			Price

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