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Cinacalcet Impurity D

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Cinacalcet Impurity D Basic information

Product Name:
Cinacalcet Impurity D
Synonyms:
  • cinacalcet iMpurity 8
  • 1-NaphthaleneMethanaMine, α-Methyl-N,N-bis[3-[3-(trifluoroMethyl)phenyl]propyl]-, (αR)-
  • (R)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)propan-1-amine
  • N-[(3-Trifluoromethyl)phenyl)propyl] Cinacalcet
  • N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]-N-[3-[3-(trifluoromethyl)phenyl]propyl]propan-1-amine
  • Cinacalcet Impurity D HCL
  • Cinacalcet USP RC B
  • Cinacalcet Impurity 5(Cinacalcet USP RC B)
CAS:
1271930-15-4
MF:
C32H31F6N
MW:
543.59
Mol File:
1271930-15-4.mol
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Cinacalcet Impurity D Chemical Properties

Boiling point:
552.2±50.0 °C(Predicted)
Density 
1.203±0.06 g/cm3(Predicted)
pka
8.40±0.50(Predicted)
InChIKey
BMWNEBVDXWCUKG-CRPMJUFNNA-N
SMILES
C(N([C@@H](C1=C2C(C=CC=C2)=CC=C1)C)CCCC1=CC=CC(C(F)(F)F)=C1)CCC1=CC=CC(C(F)(F)F)=C1 |&1:2,r|
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Cinacalcet Impurity D Usage And Synthesis

Description

Cinacalcet Impurity D is a potential byproduct or impurity in the synthesis of the drug. It is essential to study the properties and potential implications of Cinacalcet Impurity D for pharmaceutical research. Cinacalcet is a drug commonly used for the treatment of hyperparathyroidism in patients with chronic kidney disease.

Uses

N-[(3-Trifluoromethyl)phenyl)propyl] Cinacalcet (Cinacalcet USP Related Compound B) is an impurity of Cinacalcet Hydrochloride (C441800). Cinacalcet is used in clinical trial in secondary hyperparathyroidism.

Preparation

Cinacalcet hydrochloride (11 g, 0.028 mol) in toluene (150 mL) was added to potassium carbonate (7.74 g, 0.056 mol) followed by 1-(3-bromopropyl)-3-(trifluoromethyl)benzene (14.95 g, 0.056 mol) under stirring at 25-30 °C. The reaction was heated and stirred at 110-111 °C for 48 h. Upon completion of the reaction (by TLC), the reaction was cooled and quenched with water (100 mL). The organic layer was separated, washed with water (100 mL), and concentrated under reduced pressure to obtain a thick oil. The crude oil was then purified by column chromatography on silica gel by eluting with chloroform to afford Cinacalcet Impurity D as a thick transparent oil. 

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