Synthesis 2018; 50(07): 1471-1481
DOI: 10.1055/s-0036-1591882
paper
© Georg Thieme Verlag Stuttgart · New York

A Convenient Synthetic Approach to Saccharin Derivatives ­Containing a Sulfonylamidine Scaffold

a  Medicinal Chemistry, Cardiovascular and Metabolic Diseases, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: yantao.chen@astrazeneca.com
,
Carl-Johan Aurell*
b  Early Chemical Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: carl-johan.aurell@astrazeneca.com
,
Pernilla Korsgren*
c  Early Product Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: pernilla.korsgren@astrazeneca.com
,
Johanna Malm
c  Early Product Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: pernilla.korsgren@astrazeneca.com
,
Malin Härslätt
c  Early Product Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: pernilla.korsgren@astrazeneca.com
,
Maria Fridén-Saxin
d  Respiratory, Inflammation and Autoimmunity, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden
,
Anna Pettersen
c  Early Product Development, Pharmaceutical Sciences, IMED Biotech Unit, AstraZeneca, Gothenburg, Sweden   Email: pernilla.korsgren@astrazeneca.com
› Author Affiliations
Further Information

Publication History

Received: 10 November 2017

Accepted after revision: 04 December 2017

Publication Date:
11 January 2018 (online)


Abstract

A key intermediate was obtained as solid through filtration of the reaction mixture of saccharin, chloro(triphenyl)phosphonium chloride, and N,N-diisopropylethylamine (DIPEA) in chloroform. The soluble triphenylphosphine oxide went to filtrate as waste, while the solid was reacted with amines to afford N-sulfonylamidines. In total, 26 N-sulfonylamidine products were obtained in moderate to good overall yields.

Supporting Information

 
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