1207533-91-2

Upstream product

• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 1279582-34-1 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl ]prop-2-en-1-amine 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 64189-17-9 3-<3-(trifluoromethyl)phenyl>prop-2-en-1-ol 
• 402-26-6 3-(trifluoromethyl)phenylmagnesium bromide 
• 154309-48-5 1-<3-(trifluoromethyl)phenyl>prop-2-en-1-ol 
• 1273319-40-6 1-(1-chloroprop-2-en-1-yl)-3-(trifluoromethyl)benzene 
• 41412-73-1 1-[3-chloroprop-1-en-1-yl]-3-(trifluoromethyl)benzene 
• 454-89-7 3-Trifluoromethylbenzaldehyde 

Downstream Products

• 1204313-91-6 (R)-tert-butyl (1-(naphthalen-1-yl)ethyl)(3-(3-(trifluoromethyl)phenyl)propyl)carbamate 
• 1207534-31-3 C₂₇H₂₈F₃NO₂ 
• 364782-34-3 cinacalcet hydrochloride 
• 226256-56-0 cinacalcet 
• 1273319-38-2 N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine citrate 

Relevant academic research and scientific papers

A novel method for the large scale synthesis of cinacalcet hydrochloride using iron catalyzed C-C coupling

A novel synthetic route for commercial preparation of cinacalcet hydrochloride (1), a calcimimetic agent and calcium-sensing receptor antagonist, is described. Our synthetic approach involves the preparation of cinacalcet using C-C bond formation catalyzed by iron acetylacetonate/NMP complex with aryl Grignard reagent benzotrifluoride magnesium bromide (8) and alkenyl halide N-chloropropene naphthylethylamine (6).

PROCESS FOR PREPARATION OF CINACALCET INTERMEDIATE AND CINACALCET HYDROCHLORIDE

The present invention provides one pot process for preparation of highly pure unsaturated cinacalcet hydrochloride (II) comprising: i) converting 3-(trifluromethyl) cinnamic acid (III) into 3-(3-(trifluoromethyl)phenyl)prop-2-en-1-ol (IV), ii) converting 3-(3-(trifluoromethyl)phenyl)prop-2-en-1-ol (IV) to compound (V), wherein R is Cl, Br, I, tosylate and mesylate, Formula (V) iii) reacting compound (V) with (R)-1-(1-Naphthyl) ethylamine (VI) in presence of base followed by treatment with hydrochloric acid. The present invention further provides conversion of unsaturated cinacalcet hydrochloride (II) to cinacalcet hydrochloride (I).

PROCESSES FOR THE PREPARATION OF CINACALCET

The present invention provides processes and intermediates for preparing cinacalcet base and pharmaceutically acceptable salts thereof.

PROCESSES FOR THE PREPARATION OF CINACALCET

The present invention provides processes and intermediates for preparing cinacalcet base and pharmaceutically acceptable salts thereof.

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.

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.