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Cinacalcet hydrochloride
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  • Name Cinacalcet hydrochloride
  • EINECS620-490-5
  • CAS No. 364782-34-3
  • DensityN/A
  • PSA12.03000
  • LogP7.33490
  • SolubilityN/A
  • Melting Point175-177 °C
  • FormulaC22H22F3N.HCl
  • Boiling Point440.9 °C at 760 mmHg
  • Molecular Weight393.88
  • Flash Point220.5 °C
  • Transport InformationN/A
  • AppearanceOff-white to tan solid
  • Safety24/25
  • Risk CodesN/A
  • Molecular Structure
    Molecular Structure of 364782-34-3 (Cinacalcet hydrochloride)
  • Hazard SymbolsN/A
  • SynonymsN/A
  • Article Data60

Cinacalcet hydrochloride Synthetic route

1601479-86-0

(R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water for 12h; Reflux;100%
3886-70-2

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

21172-43-0

methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
Stage #1: (R)-1-(1-Naphthyl)ethylamine; methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester With potassium carbonate; potassium iodide; 1-(n-butyl)-3-methylimidazolium triflate In acetonitrile for 6h; Reflux;
Stage #2: With hydrogenchloride at 50 - 55℃; for 1h; Reagent/catalyst;		98.25%
Stage #1: (R)-1-(1-Naphthyl)ethylamine; methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester With potassium carbonate In toluene for 16h; Reflux;
Stage #2: With hydrogenchloride In water; toluene at 70℃; Reagent/catalyst; Solvent; Temperature; Time;		85%
1005450-55-4

(R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
Stage #1: (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide With sodium tetrahydroborate; iodine In tetrahydrofuran at 0 - 75℃; for 6.5h;
Stage #2: With hydrogenchloride In hexane; water for 1h;		96.22%
Stage #1: (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide With sodium tetrahydroborate; boron trifluoride In tetrahydrofuran; diethylene glycol dimethyl ether at 45 - 60℃;
Stage #2: With hydrogenchloride In toluene Further stages.;		95%
Stage #1: (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide With dodecacarbonyl-triangulo-triruthenium; 1,1,3,3-tetramethyldisilazane In toluene at 50℃; for 18h;
Stage #2: With hydrogenchloride In 1,4-dioxane at 50℃;		93%
226256-56-0

cinacalcet

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In n-heptane; ethyl acetate at 20℃;95%
With hydrogenchloride In acetonitrile at 25 - 55℃; for 0.2h;93.1%
With hydrogenchloride In n-heptane; water; toluene at 25 - 30℃; pH=1 - 2; Product distribution / selectivity;92.55%

(R)-α-methyl-N-[3-[3-trifluoromethylphenyl]propyl]-1-naphthalenemethanamine phosphate

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
Stage #1: (R)-α-methyl-N-[3-[3-trifluoromethylphenyl]propyl]-1-naphthalenemethanamine phosphate With sodium hydroxide In water; ethyl acetate at 20℃; for 1h; Inert atmosphere;
Stage #2: With hydrogenchloride In ethyl acetate at 20 - 25℃;		94%
108-05-4

vinyl acetate

57605-95-5

1-(1-naphthyl)ethanol

104774-87-0

3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
Stage #1: vinyl acetate; 1-(1-naphthyl)ethanol at 30℃; for 12h; Enzymatic reaction;
Stage #2: 3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 25℃;
Stage #3: With hydrogenchloride In water Solvent;		93.3%

cinacalcet L-tartrate

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
Stage #1: cinacalcet L-tartrate With sodium carbonate In water at 15 - 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile at 15 - 20℃; for 0.5h;		92.54%
1240705-66-1

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

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
With hydrogen; palladium dichloride In methanol; ethyl acetate at 20℃; under 750.075 Torr; for 0.5h; Product distribution / selectivity;92.5%
1207533-91-2

(R)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl-2-ene]-1-naphthalenemethaneamine hydrochloride

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In water; ethyl acetate at 25 - 30℃; Large scale;91%
With palladium 10% on activated carbon; hydrogen; potassium carbonate In methanol at 20 - 25℃; under 1500.15 - 2250.23 Torr; for 3h; pH=4.1;71%
With hydrogen; Raney nickel In methanol; ethyl acetate at 20℃; Product distribution / selectivity; Inert atmosphere;69.6%
With hydrogen; palladium(II) hydroxide In methanol at 5 - 10℃; under 1103.36 Torr; for 3h; Product distribution / selectivity; Autoclave;
Multi-step reaction with 2 steps
1.1: sodium hydrogencarbonate / ethyl acetate; water / 1 h / 20 °C / Inert atmosphere
1.2: 1 h / 20 °C / Inert atmosphere
2.1: hydrogenchloride; hydrogen / 2-5percent w/w palladium on carbon / water; methanol / 20 - 30 °C / Inert atmosphere
View Scheme
1410044-63-1

2-methylpropane-2-sulfinic acid (1-naphthalen-1-ylethyl)-[3-(3-trifluoromethylphenyl)propyl]amide

364782-34-3

cinacalcet hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In tert-butyl methyl ether; water at 20℃;91%

Cinacalcet hydrochloride Chemical Properties

Molecular Structure of Cinacalcet hydrochloride (CAS NO.364782-34-3):

IUPAC Name: N-[(1R)-1-Naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine hydrochloride 
Molecular Formula: C22H22F3N.HCl
Molecular Weight: 393.88
H-Bond Donor: 2
H-Bond Acceptor: 4 
Flash Point: 220.5 °C
Enthalpy of Vaporization: 69.81 kJ/mol
Boiling Point: 440.9 °C at 760 mmHg
Vapour Pressure: 5.67E-08 mmHg at 25 °C
Melting Point: 175-177 °C
Appearance: Off-White to Tan Solid
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals 
SMILES: FC(F)(F)c1cccc(c1)CCCN[C@@H](c3c2ccccc2ccc3)C.Cl 
InChI: InChI=1/C22H22F3N.ClH/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25;/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3;1H/t16-;/m1./s1
InChIKey: QANQWUQOEJZMLL-PKLMIRHRBW
Classification Code: Treatment of hyperparathyroidism and related disorders, such as hypercalcemia [reduction of PTH secretion through modulation of calcium ion receptors on parathyroid cells] 

Cinacalcet hydrochloride Uses

 Cinacalcet hydrochloride (CAS NO.364782-34-3) is used for clinical trial in secondary hyperparathyroidism.

Cinacalcet hydrochloride Specification

 Cinacalcet hydrochloride (CAS NO.364782-34-3), its Synonyms are 1-Naphthalenemethanamine, alpha-methyl-N-(3-(3-(trifluoromethyl)phenyl)propyl)-, (alphaR)-, hydrochloride ; AMG 073 HCl ; AMG073 HCl ; Cinacalcet HCl ; Mimpara ; N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine hydrochloride ; Regpara ; Sensipar .

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