1204313-91-6

Upstream product

• 226256-56-0 cinacalcet 
• 24424-99-5 di-tert-butyl dicarbonate 
• 78573-45-2 3-[3-(trifluoromethyl)phenyl]propan-1-ol 
• 585-50-2 3-(3-trifluoromethylphenyl)propanoic acid 
• 518335-32-5 tert-butyl (R)-1-(naphthalen-1-yl)ethylcarbamate 
• 955373-54-3 (R)-N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine 
• 402-24-4 3-(trifluoromethyl)styrene 
• 1601479-79-1 (R)-(1-(naphthalen-1-yl)ethyl)allylcarbamic acid tert-butyl ester 
• 1885-46-7 trifluoromethanesulfonic acid difluoromethyl ether 
• 61220-44-8 3-(3-chlorophenyl)propyl 4-methylbenzenesulfonate 
• 1866-38-2 3-chlorocinnamic acid 
• 21640-48-2 3-chlorohydrocinnamic acid 
• 22991-03-3 3-(3-chlorophenyl)propanol 
• 1355993-10-0 (R)-3-(3-((tert-butoxycarbonyl)(1-(naphthalen-1-yl)ethyl)amino)propyl)phenylboronic acid 

Downstream Products

• 364782-34-3 cinacalcet hydrochloride 
• 1609282-66-7 C₂₇H₂₉F₃⁽¹⁸⁾FNO₂ 

Relevant academic research and scientific papers

Cinacalcet intermediate and synthesis method of cinacalcet hydrochloride

The invention relates to a cinacalcet intermediate and a synthesis method of cinacalcet hydrochloride. The synthesis method of cinacalcet hydrochloride comprises the steps of (c) in an organic solvent, carrying out olefin metathesis reaction on a compound N-III and a compound B-2 under the action of a catalyst to obtain a compound C-I; (d) carrying out hydrogenation reduction reaction on the compound C-I to obtain a compound C-II; and (e) removing an amino protecting group from the compound C-II, and salifying with hydrogen chloride to obtain cinacalcet hydrochloride. The method has the advantages of high yield, high chemical purity and optical purity of the product, simple post-treatment process, simple and easily available raw materials, and facilitation of industrial production. The reaction formula is shown in the description, wherein R is selected from t-butyloxycarbonyl, benzoyl and carbobenzoxy.

Copper-mediated trifluoromethylation of diaryliodonium salts with difluoromethyltriflate

The reaction of diaryliodonium salts with difluoromethyltriflate in the presence of TBAT and CuTC gave the corresponding trifluoromethylated arenes in moderate yields. Compared to other difluorocarbene-derived trifluoromethylation reactions, the current one proceeded at mild reaction conditions (room temperature) within short reaction time (5 min).

Copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids using (trifluoromethyl)trimethylsilane

Trifluoromethylated acetylenes and arenes are widely applicable in the synthesis of pharmaceuticals and agrochemicals. In 2010, our group has reported the copper-mediated oxidative trifluomethylation of terminal alkynes and aryl boronic acids. This method allows a wide range of functional group tolerant trifluoromethylated acetylenes and arenes to be easily prepared. After the preliminary mechanistic studies of the oxidative trifluoromethylation of terminal alkyne, an efficient copper-catalyzed oxidative trifluoromethylation of terminal alkynes and aryl boronic acids has been developed. The catalytic protocol is successfully achieved by adding both the substrate and a portion of CF3TMS slowly using a syringe pump to the reaction mixture.

PROCESS FOR PREPARING CINACALCET AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The resent invention rovides a novel rocess for re arin cinacalcet of formula I and pharmaceutically acceptable salts thereof and process of purification. The present invention also provides novel nitrogen protected synthetic intermediates useful in the process of the present invention. Further, the present invention provides a novel substituted carbamate impurity and process of preparation thereof.

HIGHLY PURE CINACALCET OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF

Provided herein are impurities of cinacalcet, (R)-α-methyl-N-[3-[3-(trifluoromethyl) phenyl]propyl]-1-(5,6,7,8-tetrahydronaphthalene)methaneamine (tetrahydro cinacalcet impurity), (R)-α-Methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1- naphthalenemethaneamine-N-oxide (cinacalcet N-oxide impurity) and (R)-α-methyl-N-[3-[3- (trifiuoromethyl)phenyl]methyl]-1-naphthalenemethaneamine (benzylamine impurity); and processes for preparation and isolation thereof. Provided further herein is a highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities, processes for the preparation thereof, and pharmaceutical compositions comprising highly pure cinacalcet or a pharmaceutically acceptable salt thereof substantially free of impurities.

UNSATURATED CINACALCET SALTS AND PROCESSES FOR PREPARING CINACALCET HYDROCHLORIDE

Disclosed herein are convenient, industrially advantageous and environmentally friendly processes for the preparation of cinacalcet hydrochloride. Disclosed also herein are novel hydrochloride, oxalate and di-p-toluoyl-L-(+)-tartrate salts of (R)-a-methyl-N-[3-[3- (trifluoromethyl)phenyl]propylene]-l -naphthalenemethaneamine (unsaturated cinacalcet), solid state forms of the salts, and a process for their preparation thereof.

PROCESS FOR PREPARING CINACALCET AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The resent invention rovides a novel rocess for re arin cinacalcet of formula I and pharmaceutically acceptable salts thereof and process of purification. The present invention also provides novel nitrogen protected synthetic intermediates useful in the process of the present invention. Further, the present invention provides a novel substituted carbamate impurity and process of preparation thereof.