1005450-55-4

Basic information

• Product Name: N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide
• Synonyms: lN-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide;N-[1-(R)-(1-Naphthyl)ethyl]-3-[3-(trifluoromethyl)phenyl]-1-propanamide;-N-(1-(Naphthalen-1-yl);N-《R)-I-(naphthalen-I-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide;N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide;(R)-N-(1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide;N-[1-(R)-(1-Naphthyl)ethyl]-3-[3-trifluoroMethylphenyl]propanaMide
• CAS NO: 1005450-55-4
• Molecular Formula: C₂₂H₂₀F₃NO
• Molecular Weight: 371.3955096
• EINECS: -0
• Mol File: 1005450-55-4.mol
• Article Data: 16

Chemical Properties

• Melting Point: 90-92℃ (cyclohexane )
• Boiling Point: 530.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.210±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.18±0.46(Predicted)
• CAS DataBase Reference: N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide(1005450-55-4)
• EPA Substance Registry System: N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoroMethyl)phenyl)propanaMide(1005450-55-4)

Safety Data

• Hazardous Substances Data: 1005450-55-4(Hazardous Substances Data)

Usage

General Description

"N-((R)-1-(naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide" is a chemical compound with a complex molecular structure. It is an amide compound that contains a naphthalene ring, a trifluoromethyl group, and a propanamide moiety. The compound is classified as a chiral molecule, containing a stereocenter that gives rise to enantiomers with different optical activities. It may have potential applications in the field of pharmaceuticals or agrochemicals, but further research is necessary to fully understand its properties and potential uses.

Upstream product

• 3886-70-2 (R)-1-(1-Naphthyl)ethylamine 
• 455-03-8 3-(trifluoromethyl)benzenepropanoic acid chloride 
• 585-50-2 3-(3-trifluoromethylphenyl)propanoic acid 
• 82572-04-1 (R)-<1-(1-Naphthyl)ethyl>ammonium chloride 
• 1095393-66-0 (R)-N-(1-naphthalen-1-yl-ethyl)-3-(3-trifluoromethyl-phenyl)-(E)-acrylamide 
• 1076239-83-2 C₁₃H₁₃F₃O₄ 
• 1095393-72-8 3-(3-trifluoromethyl-phenyl)-propynoic acid ((R)-1-naphthalen-1-yl-ethyl)-amide 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 22561-77-9 2‐(1‐naphthalenyl)propanoic acid 
• 703-55-9 1-naphthylmagnesiumbromide 
• 90-11-9 1-Bromonaphthalene 
• 251957-73-0 1‐naphthalenylzinc bromide 
• 42882-31-5 (RS)-1-(1-naphthyl)ethylamine 

Downstream Products

• 226256-56-0 cinacalcet 
• 364782-34-3 cinacalcet hydrochloride 
• 1025064-41-8 [3-(3-difluoromethyl-phenyl)-propyl]-((R)-1-naphthalen-1-yl-ethyl)-amine 

Relevant articles and documents

Practical synthesis of the calcimimetic agent, cinacalcet

A practical synthesis of cinacalcet (Sensipar, Mimpara) is described. The synthesis starts from readily available starting materials and relies on safe and practical reaction conditions. The sequence comprises three synthetic steps and only one isolation point. The overall yield for the sequence is 85%.

Preparation method of cinacalcet hydrochloride and intermediate thereof

The invention discloses a preparation method of cinacalcet hydrochloride and an intermediate thereof. The invention provides a preparation method of an intermediate L-cinacalcet tartrate III of cinacalcet hydrochloride. The method comprises the following steps: step (1): in an organic solvent, in the presence of a chiral catalyst and a chiral ligand, an asymmetric hydrogenation reduction reactionis conducted on a cinacalcet intermediate II to obtain cinacalcet IV, wherein the chiral catalyst is bis (1, 5-cyclooctadiene)-rhodium trifluoromethanesulfonate, and the chiral ligand is (S)-3, 3'-bis(2, 4, 6-triisopropylphenyl)-1, 1'-di-2-naphthol cyclic phosphate; and (2) in an organic solvent, a neutralization reaction is conducted between cinacalcet IV and L-tartaric acid to obtain L-cinacalcet tartrate III. The preparation method disclosed by the invention has advantages of short route step, simple and safe operation and high total yield; and the prepared product has high purity, meets the requirements of bulk drugs, is low in production cost and is suitable for industrial production.

Preparation method of cinacalcet hydrochloride

The invention provides a preparation method of cinacalcet hydrochloride, which comprises the following steps: (1) reacting a compound as shown in a formula I with thionyl chloride under the conditionsthat isopropyl acetate and N, N-dimethylformamide are used as solvents and the temperature is 40-45 DEG C to obtain a product; (2) directly reacting the product obtained in the step (1) with a raw material A to obtain an intermediate I; and (3) carrying out reduction reaction and refining on the intermediate I obtained in the step (2) to obtain cinacalcet hydrochloride. According to the preparation method provided by the invention, by using isopropyl acetate and N, N-dimethylformamide (DMF) as solvents in the first-step reaction, compared with the prior art requiring the reaction conditions of higher reaction temperature and a large amount of thionyl chloride, the temperature is greatly reduced, the use amount of thionyl chloride is reduced, higher yield is still ensured, and the method has higher industrialization value.

Method for asymmetrically synthesizing (R)-cinacalcet

The invention discloses a new method for asymmetrically synthesizing (R)-cinacalcet. The method includes: taking racemic 2-bromo-propionic acid (4-methoxybenzyl) ester as a starting raw material, andbeing in asymmetric Negishi cross coupling reaction with 2-nathphyl zinc bromide under catalysis of CoI2 and chiral ligand to generate (R)-2-(1-nathphyl) propionic acid (4-methoxybenzyl) ester; beingin reaction with oxalyl chloride through LiOH reduction to generate (R)-2-(1-nathphyl) propionyl chloride; being reaction with ammonia water to generate (R)-2-(1-nathphyl) propionamide, and allowing Hofmann degradation to obtain (R)-1-nathphalene ethylamine; being in reaction with 3-(trifluoromethyl) phenylpropionic acid to generate (R)-N-(1-nathphalene ethyl)-3-(3-trifluoromethylphenyl) propionamide, and allowing LiAlH4 reduction to obtain (R)-cinacalcet. Cobalt catalyzed asymmetric Negishi cross coupling reaction is utilized for the first time to build the chiral center of (R)-cinacalcet, the method is mild in reaction condition and environment-friendly, and optical purity of (R)-cinacalcet is high (99%ee).