Development of a Multikilogram Scale Synthesis of a TRPV1 Antagonist

A highly efficient, regioselective five-step synthesis of the TRPV1 antagonist 1 is described. The coupling of piperazine 7 with dichloropyrimidine 8 proceeded via a regioselective Pd-mediated amination affording product 11 in excellent yield. Conversion of the penultimate product 14 afforded 1 thro...

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Bibliographic Details
Published inOrganic process research & development Vol. 20; no. 2; pp. 227 - 232
Main Authors Kuethe, Jeffrey T, Journet, Michel, Peng, Zhihui, Zhao, Dalian, McKeown, Arlene, Humphrey, Guy R
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 19.02.2016
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
PRACTICAL SYNTHESIS
PAIN
EFFICACY
VANILLOID RECEPTOR TRPV1
CHANNELS
EXCHANGE
DISCOVERY
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Summary:A highly efficient, regioselective five-step synthesis of the TRPV1 antagonist 1 is described. The coupling of piperazine 7 with dichloropyrimidine 8 proceeded via a regioselective Pd-mediated amination affording product 11 in excellent yield. Conversion of the penultimate product 14 afforded 1 through formation of a magnesium ate complex and trapping with CO2.
ISSN:1083-6160
1520-586X
DOI:10.1021/acs.oprd.5b00388