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J Org Chem. 2018 Aug 17;83(16):9510-9516. doi: 10.1021/acs.joc.8b01244. Epub 2018 Jul 6.

Bench-Stable Transfer Reagent Facilitates the Generation of Trifluoromethyl-sulfonimidamides.

Author information

1
Structural Genomics Consortium & Target Discovery Institute, Nuffield Department of Medicine Research Building , University of Oxford , Old Road Campus, Roosevelt Drive , Oxford OX3 7FZ , U.K.
2
Neuroscience Medicinal Chemistry , Janssen Research & Development , Turnhoutseweg 30 , B-2340 Beerse , Belgium.
3
Neuroscience Medicinal Chemistry , Janssen Research & Development , C/Jarama 75A , 45007 Toledo , Spain.

Abstract

Sulfonimidamides are an emerging bioisosteric replacement in medicinal chemistry projects, and therefore new chemistries are necessary to access this functionality. The general synthesis of CF3-sulfonimidamides from an activated bench-stable transfer reagent is described. A diverse reaction scope is demonstrated, with a wide range of nucleophilic amines being tolerated in this transformation. The CF3-sulfonimidamides obtained contain an additional diversity point, in the form a protected imine, that could be unmasked to allow late stage modifications.

PMID:
29932332
DOI:
10.1021/acs.joc.8b01244

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