1198785-20-4

Basic information

• Product Name: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol
• Synonyms: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol
• CAS NO: 1198785-20-4
• Molecular Weight: 302.312
• Mol File: 1198785-20-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol(1198785-20-4)
• EPA Substance Registry System: (S)-6-(5-fluoro-2-methylphenyl)-6-methyl-4-(trifluoromethyl)hept-1-yn-4-ol(1198785-20-4)

Safety Data

• Hazardous Substances Data: 1198785-20-4(Hazardous Substances Data)

Upstream product

• 400-31-7 1,1,1-trifluoro-4-methyl-pent-3-en-2-one 
• 866943-85-3 (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-((R)-toluene-4-sulfinylmethyl)pentan-2-ol 
• 866943-87-5 (S)-1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methyl-2-p-tolylsulfanylmethylpentan-2-ol 
• 1066-54-2 trimethylsilylacetylene 
• 129217-85-2 trimethyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-1-yn-1-yl)silane 
• 54655-07-1 lithium trimethylsilylacetylenide 

Relevant articles and documents

Synthesis of two potent glucocorticoid receptor agonists labeled with carbon-14 and stable isotopes

Two potent glucocorticoid receptor agonists were prepared labeled with carbon-14 and with stable isotopes to perform drug metabolism, pharmacokinetics, and bioanalytical studies. Carbon-14 labeled (1) was obtained from an enantiopure alkyne (5) via a Sonogashira coupling to a previously reported 5-amino-4-iodo-[2-14C]pyrimidine [14C]-(6), followed by a base-mediated cyclization (1) in 72% overall radiochemical yield. Carbon-14 labeled (2) was prepared in five steps employing a key benzoic acid intermediate [14C]-(13), which was synthesized in one pot from enolization of trifluoromethylketone (12), followed by bromine-magnesium exchange and then electrophile trapping reaction with [14C]-carbon dioxide. A chiral auxiliary (S)-1-(4-methoxyphenyl)ethylamine was then coupled to this acid to give [14C]-(15). Propargylation and separation of diastereoisomers by crystallizations gave the desired diastereomer [14C]-(17) in 34% yield. Sonogashira coupling to iodopyridine (10) followed by cyclization to the azaindole [14C]-(18) and finally removal of the chiral auxiliary gave [14C]-(2) in 7% overall yield. For stable isotope syntheses, [13C6]-(1) was obtained in three steps using [13C4]-(6) and trimethylsilylacetylene-[13C2] in 26% yield, while [2H5]-(2) was obtained by first preparing the iodopyridine [2H5]-(10) in five steps. Then, Sonogashira coupling to chiral alkyne (24) and cyclization gave [2H5]-(2) in 42% overall yield.

GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF

Compounds of Formula I wherein R1, R2, X, and Y are as defined herein, or a tautomer, optical isomer, prodrug, co-crystal, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.