Cinacalcet supplier | CasNO.226256-56-0

Name
CINACALCET
EINECS 682-701-7
CAS No. 226256-56-0
Article Data61
CAS DataBase
Density 1.154 g/cm³
Solubility
Melting Point
Formula C₂₂H₂₂F₃N
Boiling Point 440.9 °C at 760 mmHg
Molecular Weight 357.419
Flash Point 220.5 °C
Transport Information
Appearance yellow oil
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms AMG073;Cinacalcet;
PSA 12.03000
LogP 6.53290

Synthetic route

: 1073144-62-3
(1R)-1-(naphthalen-1-yl)ethanamine (R)-mandelate

: 21172-43-0
methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With potassium carbonate In water at 60 - 65℃; for 20h;	100%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 78573-45-2
3-[3-(trifluoromethyl)phenyl]propan-1-ol

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; D-sorbitol; choline chloride at 60℃; for 12h;	98%
Stage #1: 3-[3-(trifluoromethyl)phenyl]propan-1-ol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; Stage #2: (R)-1-(1-Naphthyl)ethylamine With sodium tris(acetoxy)borohydride In dichloromethane optical yield given as %ee;	84%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 17h; Inert atmosphere; Sealed tube;	75%
With C19H22MnN3O3P(1+); potassium hydride In 1,2-dimethoxyethane at 100℃; for 48h; Glovebox; Sealed tube; Inert atmosphere;	50%

: 364782-34-3
cinacalcet hydrochloride

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium carbonate In dichloromethane; water	96%
With water; sodium carbonate In di-isopropyl ether at 25℃; for 2.25h; pH=9.5;

: (R)-cinacalcet (-)-di-para-D-toluoyl tartrate

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water for 0.5h; pH=9 - 10;	96%

: 98-08-8
α,α,α-trifluorotoluene

: (R)-3-bromo-N-(1-(naphthalen-1-yl)ethyl)propan-1-amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0℃; for 2h;	95.6%

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

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol under 1520.1 Torr; for 2h; Pressure;	95%
With hydrogen; palladium on activated carbon In methanol for 14h; Product distribution / selectivity;	90%
With hydrogen; 5%-palladium/activated carbon In toluene at 10 - 30℃; under 152.01 - 1140.08 Torr; Industry scale;	79.4%

: 1201910-95-3
(R)-N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino]-N-[1-(1-naphthyl)ethylamine]

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogen In ethanol at 80℃; under 7500.75 Torr; for 3h; High pressure;	95%

: 566938-58-7
1-(3-iodopropyl)-3-(trifluoromethyl)benzene

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃; for 12h;	95%

: (R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogenchloride; zinc In water at 20℃; pH=< 1;	94.1%
With hydrazine hydrate; potassium hydroxide In ethanol at 90 - 180℃; for 2h; Solvent;	83.5%

: 941-98-0
1'-naphthacetophenone

: 104774-87-0
3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With titanium(IV) isopropylate; hydrogen; 1,8-diazabicyclo<5.4.0>undec-7-ene hidrochloride In acetic acid methyl ester at 50℃; under 38002.6 Torr; for 20h; Reagent/catalyst; Solvent; stereoselective reaction;	94%

: 1095393-66-0
(E)-N-((R)-1-naphthalen-1-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-acrylamide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
Stage #1: (R)-N-(1-naphthalen-1-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-(E)-acrylamide With dimethylsulfide borane complex In toluene at 50℃; for 3h; Stage #2: With hydrogenchloride; water In toluene at 50℃; for 1h; Product distribution / selectivity;	93%
With diisobutylaluminium hydride In dichloromethane; toluene at 50℃; for 1.5h; Product distribution / selectivity;	60%
Stage #1: (R)-N-(1-naphthalen-1-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-(E)-acrylamide With lithium aluminium tetrahydride In tetrahydrofuran at 64℃; for 23.3333h; Stage #2: With water; ethyl acetate In tetrahydrofuran at 0 - 10℃; for 0.25h; Product distribution / selectivity;
Stage #1: (R)-N-(1-naphthalen-1-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-(E)-acrylamide With sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 30 - 55℃; for 8h; Stage #2: With water; Rochelle's salt In toluene at 5℃; for 0.75h; Product distribution / selectivity;

: (1R)‐1‐(naphthalen‐1‐yl)ethyl 4‐methylbenzene‐1‐sulfonate

: 104774-87-0
3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 5h;	93%

: 1005450-55-4
(R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h;	92%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 10h; Schlenk technique; Inert atmosphere;	92%
With borane-ammonia complex; boron trifluoride diethyl etherate; tris(pentafluorophenyl)borate In 1,2-dichloro-ethane at 60℃;	83%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 21172-41-8
3-[3-(trifluoromethyl)phenyl]propanal

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
Stage #1: (R)-1-(1-Naphthyl)ethylamine; 3-[3-(trifluoromethyl)phenyl]propanal With tris(pentafluorophenyl)borate In toluene at 20℃; Molecular sieve; Stage #2: With ammonia borane In toluene at 20℃; for 12h; Molecular sieve; enantioselective reaction;	92%
Stage #1: (R)-1-(1-Naphthyl)ethylamine; 3-[3-(trifluoromethyl)phenyl]propanal In tetrahydrofuran for 0.25h; Stage #2: With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran for 2h; Stage #3: With sodium carbonate In dichloromethane; water Product distribution / selectivity;	89%
With triethylsilane; palladium on carbon; TPGS-750-M In water at 45℃; for 7h;	88%

: 941-98-0
1'-naphthacetophenone

: 104774-93-8
3-(3-trifluoromethyl-phenyl)-propylamine hydrochloride

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With titanium(IV) isopropylate; hydrogen In ethyl acetate at 50℃; under 38002.6 Torr; for 20h; stereoselective reaction;	91%

: 1‐[(1R)‐1‐bromoethyl]naphthalene

: 104774-87-0
3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With triethylamine In methanol at 20℃; for 3h;	90%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 585-50-2
3-(3-trifluoromethylphenyl)propanoic acid

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 120℃; for 24h; Solvent; Reagent/catalyst; Concentration; Inert atmosphere; Schlenk technique;	89%
With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 120℃; for 20h; Schlenk technique; Inert atmosphere;	87%
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 36h; Glovebox; Molecular sieve; Schlenk technique;

: 1025949-34-1
(1R)‐1‐(naphthalen‐1‐yl)ethyl methanesulfonate

: 104774-87-0
3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 8.5h;	86%

: (R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propane-2,3-dione

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium tetrahydroborate; boron trifluoride diethyl etherate In tetrahydrofuran at 50 - 60℃; for 3h; Reagent/catalyst; Temperature; Flow reactor;	83.5%

: 826-74-4
1-vinylnaphthalene

: N,N-dimethyl-4-((((3-(3-(trifluoromethyl)phenyl)propyl)amino)oxy)carbonyl)aniline

A: (S)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine

B: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With diethoxymethylane; (S)-DTBM-SEGPHOS; copper diacetate; triphenylphosphine In tetrahydrofuran at 20℃; for 16h; Inert atmosphere; Glovebox; enantioselective reaction;	A n/a B 82%

...Expand

: ((1R)-1-(1-naphthyl)ethyl) N-(3-(3-(trifluoromethyl)phenyl)propyl)-o-nitrobenzenesulfonamide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With lithium hydroxide monohydrate In N,N-dimethyl-formamide; toluene at 25℃; for 2h;	81%
With lithium hydroxide monohydrate; mercaptoacetic acid In acetonitrile Inert atmosphere; Reflux; Autoclave; Large scale;

: (R)-1-(naphthalen-2-yl)-N-(3-(3-(trifluoromethyl)phenyl)-propylidene)ethanamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With C46H36BF10P; hydrogen In toluene at 40℃; under 150015 Torr; for 8h; Autoclave; Inert atmosphere;	80%

: 129254-76-8
1-(3-bromopropyl)-3- (trifluoromethyl)benzene

: 154318-44-2
(1R)-1-(1-naphthyl)-N-(phenylmethylene)ethanamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
Stage #1: 1-(3-bromopropyl)-3- (trifluoromethyl)benzene; (1R)-1-(1-naphthyl)-N-(phenylmethylene)ethanamine With potassium iodide at 120 - 130℃; Stage #2: With hydrogenchloride; water In acetonitrile at 25 - 35℃; for 1h; pH=1 - 2; Stage #3: With ammonia In water pH=9 - 10; Product distribution / selectivity;	71%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 3-(3-trifluoromethylphenyl)propanoyl succinimide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
Stage #1: (R)-1-(1-Naphthyl)ethylamine; 3-(3-trifluoromethylphenyl)propanoyl succinimide In tetrahydrofuran at 20℃; Inert atmosphere; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 48h; Reflux;	57%

: 402-24-4
3-(trifluoromethyl)styrene

: 201230-82-2
carbon monoxide

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogen; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In methanol; toluene at 125℃; for 8h; Product distribution / selectivity;	53.8%

...Expand

: 1095393-72-8
3-(3-trifluoromethyl-phenyl)-propynoic acid ((R)-1-naphthalen-1-yl-ethyl)-amide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
Stage #1: 3-(3-trifluoromethyl-phenyl)-propynoic acid ((R)-1-naphthalen-1-yl-ethyl)-amide With dimethylsulfide borane complex In toluene at 50℃; for 7h; Stage #2: With hydrogenchloride; water In methanol; toluene at 90℃; for 4h; Product distribution / selectivity;	22%

: 955373-56-5
(2E)-N-[(1R)-1-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon at 20℃; under 760.051 Torr; for 16h;
With formic acid; palladium dichloride In ethanol for 5h; Product distribution / selectivity; Reflux;

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 82258-76-2
1-(3-chloropropyl)-3-(trifluoromethyl)benzene

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 81.7℃; for 5 - 22h; Product distribution / selectivity; Heating / reflux;
With potassium carbonate In water; toluene at 85℃; for 20h; Product distribution / selectivity;
With potassium carbonate In toluene for 14h; Product distribution / selectivity; Heating / reflux;
Stage #1: (R)-1-(1-Naphthyl)ethylamine; 1-(3-chloropropyl)-3-(trifluoromethyl)benzene With potassium carbonate In toluene at 80℃; for 12h; Stage #2: With tetrabutylammomium bromide In toluene at 80℃; for 1h; Product distribution / selectivity;

: N-[1-(R)-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1-propanamide

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran for 4h; Heating;

: 226256-56-0
cinacalcet

: 64-19-7
acetic acid

: 1025064-29-2
N-[1-(R)-(-)-(1-naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1-aminopropane acetate

Conditions

Conditions	Yield
In 2-methylpropyl acetate; water at 20℃; for 5.5h;	99.8%
In water; isopropyl alcohol Product distribution / selectivity;	88%
In water; toluene at 30℃; for 3.5h;

: 226256-56-0
cinacalcet

: 364782-34-3
cinacalcet hydrochloride

Conditions

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%

: 226256-56-0
cinacalcet

: cinacalcet hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 50℃; for 5h; Temperature;	94.7%

: 226256-56-0
cinacalcet

: 50893-53-3
carbonochloridic acid 1-chloro-ethyl ester

: 1301700-82-2
1-chloroethyl carbamate cinacalcet

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	94%

: 226256-56-0
cinacalcet

: 34301-54-7
1-Adamantanethiol

: C32H36F3NS3

Conditions

Conditions	Yield
Stage #1: 1-Adamantanethiol With C20H18N2O4S4 In dichloromethane at 0℃; for 0.0833333h; Stage #2: cinacalcet With dmap In dichloromethane at 0 - 20℃; for 1h;	90%

: 226256-56-0
cinacalcet

: 124-38-9
carbon dioxide

: 1206633-38-6
(R)-N-methyl-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine

Conditions

Conditions	Yield
With 3-benzyl-5-(2-hydroxy-ethyl)-4-methyl-thiazolium betaine In N,N-dimethyl acetamide at 100℃; under 760.051 Torr;	83%
With diphenylsilane; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; chemoselective reaction;	78%
With cyclopentadienyl iron(II) dicarbonyl dimer; phenylsilane; triphenylphosphine In acetonitrile at 100℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube;	70%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 100℃; under 760.051 Torr; for 48h; Schlenk technique;	54%

: 226256-56-0
cinacalcet

: 124-38-9
carbon dioxide

: 75-03-6
ethyl iodide

: C25H26F3NO2

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃; chemoselective reaction;	82%

...Expand

: 226256-56-0
cinacalcet

: 87-69-4
L-Tartaric acid

: cinacalcet L-tartrate

Conditions

Conditions	Yield
In ethanol at 5 - 65℃; for 0.5h;	80.22%

Cinacalcet Chemical Properties

IUPAC Name: N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine
Molecular Formula: C₂₂H₂₂F₃N
Molecular Weight: 357.41 g/mol
Canonical SMILES: CC(C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F
InChI: InChI=1S/C22H22F3N/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/t16-/m1/s1
Classification Code: Calcimimetic; Treatment of hyperparathyroidism and related disorders, such as hypercalcemia; Treatment of hyperthyroidism
Product Categories: Chiral Reagents;Intermediates & Fine Chemicals; Pharmaceuticals
XLogP3-AA: 6.1
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 6
Exact Mass: 357.170434
MonoIsotopic Mass: 357.170434
Topological Polar Surface Area: 12
Heavy Atom Count: 26
Complexity: 422
Molar Volume: 309.6 cm³
Polarizability: 39.88 10-24 cm³
Surface Tension: 36.8 dyne/cm
Density: 1.154 g/cm³
Flash Point: 220.5 °C
Enthalpy of Vaporization: 69.81 kJ/mol
Boiling Point: 440.9 °C at 760 mmHg
Vapour Pressure of Cinacalcet (CAS NO.226256-56-0): 5.67E-08 mmHg at 25 °C

Cinacalcet Uses

Cinacalcet (CAS NO.226256-56-0) is the first calcimimetic drug approved by the United States Food and Drug Administration for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease. Cinacalcet is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis and hypercalcemia in patients with parathyroid carcinoma.

Cinacalcet Specification

Cinacalcet (CAS NO.226256-56-0), its Synonyms are 1-Naphthalenemethanamine, alpha-methyl-N-(3-(3-(trifluoromethyl)phenyl)propyl)-, (alphaR)- ; N-((1R)-1-(1-Naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine ; N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine ; Mimpara . It is yellow oil.

Product Name

CINACALCET

Synthetic route

Cinacalcet Chemical Properties

Cinacalcet Uses

Cinacalcet Specification

Related Products

Hot Products