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| CAS No.: | 364782-34-3 |
|---|---|
| Name: | Cinacalcet hydrochloride |
| Article Data: | 60 |
| Molecular Structure: | |
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| Formula: | C22H22F3N.HCl |
| Molecular Weight: | 393.88 |
| Synonyms: | Mimpara;Regpara;Sensipar;1-Naphthalenemethanamine,a-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-,hydrochloride, (aR)-(9CI); |
| EINECS: | 620-490-5 |
| Melting Point: | 175-177 °C |
| Boiling Point: | 440.9 °C at 760 mmHg |
| Flash Point: | 220.5 °C |
| Appearance: | Off-white to tan solid |
| Safety: | 24/25 |
| PSA: | 12.03000 |
| LogP: | 7.33490 |
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(R)-N-(1-(naphthalen-1-yl)ethyl)-N-(3-(3-(trifluoromethyl)phenyl)propyl)formamide
- 364782-34-3
cinacalcet hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
- 364782-34-3
cinacalcet hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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% |
- 364782-34-3
cinacalcet hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride In tert-butyl methyl ether; water at 20℃; | 91% |
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Chemistry
Molecular Structure of Cinacalcet hydrochloride (CAS NO.364782-34-3):
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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]
Uses
Cinacalcet hydrochloride (CAS NO.364782-34-3) is used for clinical trial in secondary hyperparathyroidism.
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 .