Remote electronic control in the regioselective reduction of succinimides: A practical, scalable synthesis of EP4 antagonist MF-310

Journal of Organic Chemistry

Volumn 74, Issue 17, 2009, Pages 6863-6866

  Molinaro, Carmela ^a   Gauvreau, Danny ^a   Hughes, Gregory ^a   Lau, Stephen ^a   Lauzon, Sophie ^a   Angelaud, Rémy ^a   O'Shea, Paul D ^a   Janey, Jacob ^b   Palucki, Michael ^b   Hoerrner, Scott R ^b   Raab, Conrad E ^b   Sidler, Rick R ^b   Belley, Michel ^a   Han, Yongxin ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CHROMATOGRAPHY-FREE SYNTHESIS; CHRONIC INFLAMMATION; CYCLOPROPANATION; ELECTRONIC CONTROLS; KEY FEATURE; PYRIDINE RINGS; REGIOSELECTIVE REDUCTION; SCALABLE SYNTHESIS; SODIUM SALT; SUCCINIMIDE; SYNTHETIC ROUTES;

CARBOXYLATION; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; ELECTRONIC PROPERTIES; ELECTRONICS INDUSTRY; ORGANIC ACIDS; POWER ELECTRONICS; PROPANE; SULFUR COMPOUNDS;

PYRIDINE;

CARBOXYLIC ACID DERIVATIVE; CYCLOPROPANE; MF 310; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; PYRIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; CHRONIC INFLAMMATION; CYCLOPROPANATION; DRUG SYNTHESIS; QUANTUM YIELD; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

CARBOXYLIC ACIDS; CHEMISTRY, ORGANIC; CHEMISTRY, PHARMACEUTICAL; CRYSTALLIZATION; CYCLOPROPANES; DRUG DESIGN; ELECTRONICS; HETEROCYCLIC COMPOUNDS, 3-RING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; RECEPTORS, PROSTAGLANDIN E; STEREOISOMERISM; SUCCINIMIDES; SULFONAMIDES; TECHNOLOGY, PHARMACEUTICAL;

EID: 69549126461     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901267x     Document Type: Article

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24. A total of 5A% of minor unidentified byproduct was also observed.
25. 3Si/TFA conditions providing products 24, 25, and 26.
26. Measured pKa for MF-310 is 5.6.