cinacalcet iMpurity 4

Base Information

• Chemical Name: cinacalcet iMpurity 4
• CAS No.: 955373-56-5
• Molecular Formula: C22H20F3N
• Molecular Weight: 355.403
• Mol file: 955373-56-5.mol

Synonyms:cinacalcet iMpurity 4;1-NaphthaleneMethanaMine, α-Methyl-N-[(2E)-3-[3-(trifluoroMethyl)phenyl]-2-propen-1-yl]-, (αR)-;2,3,-Dehydro-cinacalcet;3-(3-(Trifluoromethl)phenyl-N-(R)-1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine hydrochloride

Chemical Property of cinacalcet iMpurity 4

Chemical Property:

• Boiling Point: 468.8±45.0 °C (760 mmHg)
• PSA: 12.03000
• Density: 1.179±0.06 g/cm3 (20 °C, 760 mmHg)
• LogP: 6.61350
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99%min. ^*data from raw suppliers

(E)-2,3,-Dehydro-cinacalcet ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (E)-2,3,-Dehydro-cinacalcet is an impurity of Cinacalcet Hydrochloride (C441800). Cinacalcet is used in clinical trial in secondary hyperparathyroidism.

Technology Process of cinacalcet iMpurity 4

There total 8 articles about cinacalcet iMpurity 4 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

1-[(1E)-3-bromopropyl-1-en-1-yl]-3-(trifluoromethyl)benzene + (R)-1-(1-Naphthyl)ethylamine (3886-70-2) → (2E)-N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine (955373-56-5)

Guidance literature:

(R)-1-(1-Naphthyl)ethylamine; With benzaldehyde; at 25 - 30 ℃;

1-[(1E)-3-bromopropyl-1-en-1-yl]-3-(trifluoromethyl)benzene; In 1-methyl-pyrrolidin-2-one; at 125 - 130 ℃; for 12h;

With hydrogenchloride; water; In toluene; pH=0.5 - 1.5;

Reference yield:

3-{[(1R)-1-(naphthalen-1-yl)ethyl]amino}-1-[3-(trifluoromethyl)phenyl]propan-1-one hydrochloride (1224567-99-0) → cinacalcet (226256-56-0,694495-47-1) + (2E)-N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine (955373-56-5)

Guidance literature:

With hydrogenchloride; zinc; In methanol; water; at 20 ℃; for 5h;

Reference yield:

3-bromo-1-trifluoromethylbenzene (401-78-5) + (R)-N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine (955373-54-3) → (2E)-N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine (955373-56-5)

Guidance literature:

With potassium carbonate; 2% Pd/C; In 1-methyl-pyrrolidin-2-one; at 140 ℃; for 3h;

upstream raw materials:

3-bromo-1-trifluoromethylbenzene

(R)-N-(1-(naphthalen-1-yl)ethyl)prop-2-en-1-amine

(E)-3-(3-(trifluoromethyl)phenyl)allyl acetate

(R)-1-(1-Naphthyl)ethylamine

Downstream raw materials:

cinacalcet

N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride

cinacalcet hydrochloride

Refernces

• 1、 -. "Method For The Preparation Of Cinacalcet And Intermediates And Impurities Thereof". Page/Page column 19. . Retrieved 2012/01/13.
• 2、 -. "PROCESS FOR PREPARING CINACALCET". Page/Page column 29-30. . Retrieved 2010/05/14.