The Discovery and Development of a Safe, Practical Synthesis of ABT-869

The Discovery and Development of a Safe, Practical Synthesis of ABT-869

The discovery, development and implementation of two chemical routes to ABT-869 is reported. Optimization of the first-generation heterocycle formation and Suzuki coupling is briefly described. Key features of the second-generation synthesis include the development of a safe hydrazine condensation b...

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Veröffentlicht in:Organic process research & development 2009-11, Vol.13 (6), p.1419-1425
Hauptverfasser: Kruger, Albert W, Rozema, Michael J, Chu-Kung, Alexander, Gandarilla, Jorge, Haight, Anthony R, Kotecki, Brian J, Richter, Steven M, Schwartz, Albert M, Wang, Zhe
Format: Artikel
Sprache:eng
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Zusammenfassung:The discovery, development and implementation of two chemical routes to ABT-869 is reported. Optimization of the first-generation heterocycle formation and Suzuki coupling is briefly described. Key features of the second-generation synthesis include the development of a safe hydrazine condensation by utilizing an inorganic base to increase the onset temperature of exothermic decomposition. The second-generation Suzuki reaction is discussed in detail, culminating in the use of an oxygen monitor as a PAT to maximize reproducibility on scale.
ISSN:1083-6160
1520-586X
DOI:10.1021/op900208y