A Next Generation Synthesis of BACE1 Inhibitor Verubecestat (MK-8931)

Org Lett. 2018 Mar 16;20(6):1568-1571. doi: 10.1021/acs.orglett.8b00259. Epub 2018 Feb 26.

Abstract

The development of a commercial manufacturing route to verubecestat (MK-8931) is described, highlights of which include the application of a continuous processing step to outcompete fast proton transfer in a Mannich-type ketimine addition, a copper-catalyzed amidation reaction, and an optimized guanidinylation procedure to form the key iminothiadiazine dioxide core.

MeSH terms

  • Amyloid Precursor Protein Secretases
  • Aspartic Acid Endopeptidases
  • Catalysis
  • Copper
  • Cyclic S-Oxides / chemical synthesis*
  • Enzyme Inhibitors
  • Molecular Structure
  • Thiadiazines / chemical synthesis*

Substances

  • Cyclic S-Oxides
  • Enzyme Inhibitors
  • Thiadiazines
  • Copper
  • Amyloid Precursor Protein Secretases
  • Aspartic Acid Endopeptidases
  • verubecestat