608141-44-2

Basic information

• Product Name: (R)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide
• Synonyms: (R)-Apremilast
• CAS NO: 608141-44-2
• Molecular Formula: C₂₂H₂₄N₂O₇S
• Molecular Weight: 460.50016
• EINECS: -0
• Mol File: 608141-44-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 741.3±60.0 °C(Predicted)
• Appearance: /
• Density: 1.381±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.01±0.20(Predicted)
• CAS DataBase Reference: (R)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide(608141-44-2)
• EPA Substance Registry System: (R)-N-(2-(1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl)acetamide(608141-44-2)

Safety Data

• Hazardous Substances Data: 608141-44-2(Hazardous Substances Data)

Usage

Uses

(R)-Apremilast is an enantiomer of Apremilast (A729700), an oral phosphodiesterase 4 inhibitor is used in the treatment of psoriatic arthritis.

Upstream product

• 6296-53-3 3-acetylaminophthalic anhydride 
• 608142-27-4 (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)-ethylamine 
• 603-62-3 4-nitro-1H-isoindole-1,3(2H)-dione 
• 915201-13-7 (3-ethoxy-4-methoxyphenyl)boronic acid 
• 641-70-3 3-nitrophthalic acid anhydride 
• 60758-86-3 3-ethoxy-4-methoxybenzenecarbonitrile 
• 253168-94-4 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine 
• 90-05-1 2-methoxy-phenol 
• 2518-24-3 3-aminophthalimide 
• 52849-52-2 1-Bromo-3-ethoxy-4-methoxybenzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 66037-04-5 1-acetoxy-5-bromo-2-methoxybenzene 
• 613-70-7 2-methoxyphenyl acetate 
• 1450657-28-9 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one 

Relevant articles and documents

Methods for preparation of apremilast

The present invention discloses a method for preparation of Apremilast. β-phthalimino vinylsulfones are reacted through the asymmetric addition reaction to form an addition product, and the drug of Apremilast can be obtained from the addition product through simple reactions. The method is a process for synthesizing Apremilast in a more efficient way.

Asymmetric Synthesis of β-Aryl β-Imido Sulfones Using Rhodium Catalysts with Chiral Diene Ligands: Synthesis of Apremilast

A chiral rhodium(I)-diene catalyst enabled the one-step synthesis of β-aryl β-imido sulfones under mild reaction conditions. By selection of the chiral diene ligand L1a or L2, each enantiomer of the chiral β-aryl β-imido sulfone target can be accessed with high stereoselectivity. Demonstration of the scope of the reaction, which includes the synthesis of an N-protected chiral β-amino β-phenyl sulfone, culminated with the efficient synthesis of the heteroatom-rich active pharmaceutical ingredient apremilast.

A SYNTHETIC PATHWAY TOWARDS APREMILAST

The present invention relates to an asymmetric process for providing N-{2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide (apremilast) or a pharmaceutically acceptable salt or solvate thereof.