A PRACTICAL SYNTHESIS OF NOVEL RHO-KINASE INHIBITOR, (S)-4-FLUORO-5-(2-METHYL-1,4-DIAZEPAN-1-YLSULFONYL)- ISOQUINOLINE

A practical synthesis of novel Rho-kinase inhibitor, (S)-4-fluoro-5-(2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline hydrochloride dihydrate (1) was achieved in a pilot-scale production. We have demonstrated the regioselective chlorosulfonylation of 4-fluoroisoquinoline in an one-pot reaction to aff...

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Bibliographic Details
Published inHeterocycles Vol. 83; no. 8; pp. 1771 - 1781
Main Authors Gomi, Noriaki, Ohgiya, Tadaaki, Shibuya, Kimiyuki, Katsuyama, Jyunji, Masumoto, Masayuki, Sakai, Hitoshi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 2011
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
FASUDIL
Large-Scale Production
Mitsunobu Reaction
Chlorosulfonylation
Rho-Kinase Inhibitor
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Summary:A practical synthesis of novel Rho-kinase inhibitor, (S)-4-fluoro-5-(2-methyl-1,4-diazepan-1-ylsulfonyl)isoquinoline hydrochloride dihydrate (1) was achieved in a pilot-scale production. We have demonstrated the regioselective chlorosulfonylation of 4-fluoroisoquinoline in an one-pot reaction to afford 4-fluoroisoquinoline-5-sulfonyl chloride and the asymmetric construction of the (S)-2-methyl-1,4-diazepane moiety as key steps.
ISSN:0385-5414
1881-0942
DOI:10.3987/COM-11-12230