Alternative synthesis of the anti-baldness compound RU58841Electronic supplementary information (ESI) available. CCDC 892388, 893326, 894556 and 904089. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4ra00332b

RU58841 is active against baldness and is commercially available. The previously reported synthesis uses phosgene, three discrete inert atmosphere steps and three steps that require flash chromatography. Our synthesis uses no phosgene, only one inert atmosphere step and does not require flash chroma...

Full description

Saved in:
Bibliographic Details
Main Authors Leonard, Matthew J, Lingham, Anthony R, Niere, Julie O, Jackson, Neale R. C, McKay, Peter G, Hügel, Helmut M
Format Journal Article
LanguageEnglish
Published 17.03.2014
Online AccessGet full text

Cover

More Information
Summary:RU58841 is active against baldness and is commercially available. The previously reported synthesis uses phosgene, three discrete inert atmosphere steps and three steps that require flash chromatography. Our synthesis uses no phosgene, only one inert atmosphere step and does not require flash chromatography. This is achieved by stepwise construction of the hydantoin moiety around the amino group of 3-trifluoromethyl-4-cyanoaniline and ring closure to give a 2-nitropropane leaving group. On a small scale we achieved an overall yield of 33%. A bromine-nitro substitution at tertiary carbon and using 2-nitropropane as leaving group enable a short phosgene-free synthesis of RU58841 .
Bibliography:Electronic supplementary information (ESI) available. CCDC
For ESI and crystallographic data in CIF or other electronic format see DOI
10.1039/c4ra00332b
904089
and
892388
894556
,
893326
ISSN:2046-2069
DOI:10.1039/c4ra00332b