Highly efficient synthesis of HIV NNRTI doravirine

Org Lett. 2015 Mar 20;17(6):1353-6. doi: 10.1021/ol503625z. Epub 2015 Mar 9.

Abstract

The development of an efficient and robust process for the production of HIV NNRTI doravirine is described. The synthesis features a continuous aldol reaction as part of a de novo synthesis of the key pyridone fragment. Conditions for the continuous flow aldol reaction were derived using microbatch snapshots of the flow process.

MeSH terms

  • Aldehydes / chemistry
  • HIV Infections / drug therapy*
  • HIV Reverse Transcriptase / antagonists & inhibitors*
  • Molecular Structure
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry
  • Pyridones / pharmacology
  • Reverse Transcriptase Inhibitors / chemical synthesis*
  • Reverse Transcriptase Inhibitors / chemistry
  • Reverse Transcriptase Inhibitors / pharmacology
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry
  • Triazoles / pharmacology

Substances

  • Aldehydes
  • Pyridones
  • Reverse Transcriptase Inhibitors
  • Triazoles
  • 3-hydroxybutanal
  • doravirine
  • HIV Reverse Transcriptase