608142-27-4

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethylamine is used as a key intermediate in the synthesis of Apremilast, a potent and active tumor necrosis factor (TNF) inhibitor. Apremilast is a small molecule that selectively inhibits TNF production, which is a critical mediator of inflammation and a target for the treatment of various inflammatory diseases, such as psoriasis and rheumatoid arthritis. (R)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethylaMine's unique structure allows it to effectively modulate the immune response and provide therapeutic benefits in these conditions.

Upstream product

• 253168-94-4 2-(3-ethoxy-4-methoxyphenyl)-1-(methylsulfonyl)eth-2-ylamine 
• 121-32-4 4-hydroxy-3-ethoxybenzaldehyde 
• 60758-79-4 3-ethoxy-4-hydroxybenzonitrile 
• 60758-86-3 3-ethoxy-4-methoxybenzenecarbonitrile 
• 1450657-31-4 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine 
• 608142-28-5 (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine N-acetyl-D-leucine salt 
• 1131-52-8 3-ethoxy-4-methoxybenzaldehyde 
• 621-59-0 isovanillin 

Downstream Products

• 608141-44-2 R-Apremilast 
• 635705-72-5 4-amino-2-[(1S)-1-(3-ethoxy 4-methoxyphenyl)-2-methanesulfonylethyl]-2,3-dihydro-1H-isoindole-1,3-dione 
• 608141-41-9 Apremilast 
• 608141-42-0 (S)-2-[1 (3-ethoxy-4-methoxyphenyl)]-1-methanesulfonyl-2-ethylamine 
• 1450657-31-4 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine 

Relevant academic research and scientific papers

Synthesis method of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl) ethylamine

The invention relates to a synthetic method of (S)-1-(3-ethoxy-4-methoxy phenyl)-2-(methylsulfonyl) ethylamine. The method comprises the following steps: mixing 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl) vinylamine, a chiral catalyst, an acid and a solvent, and performing reacting; the structural formula of the chiral catalyst is shown as a formula (I), wherein R is selected from a hydrogen atom, an alkyl group, an aromatic ring, an alkoxy group, a halogen atom, an amino group, a cyano group, a hydroxyl group, a trifluoromethyl group, a nitro group, an ester group or an amido group. (S)-1-(3-ethoxy-4-methoxy phenyl)-2-(methylsulfonyl) ethylamine with high chiral purity can be generated in one step, meanwhile, the product is easy to separate and purify, and the yield is high. In addition, the method is mild in reaction condition, stable in process, simple and safe in reaction operation, low in production cost, simple and feasible in three-waste treatment, environment-friendly, easily available in raw materials, low in production cost and suitable for industrial production.

Synthesis of Substituted β-Functionalised Styrenes by Microwave-Assisted Olefin Cross-Metathesis and Scalable Synthesis of Apremilast

Preparation of diversely substituted β-functionalised styrenes by microwave-assisted olefin cross-metathesis (CM) is described. This method can be also employed in the synthesis of β-deuterated α,β-unsaturated sulfones from inexpensive allylbenzenes, though unprecedented one-pot isomerisation/deuteration/cross-metathesis sequence. One of such obtained CM products has been utilised in a new scalable synthesis of Apremilast (6), a potent and orally active phosphodiesterase 4 and tumour necrosis factor-α inhibitor. The same strategy was used in synthesis of an optical antipode of 6, ent-Apremilast.

IMPROVED PROCESS FOR THE PREPARATION OF APREMILAST

The present invention relates to an improved process for the preparation of Apremilast of formula (I).

A METHOD OF CHIRAL RESOLUTION OF THE KEY INTERMEDIATE OF THE SYNTHESIS OF APREMILAST AND ITS USE FOR THE PREPARATION OF PURE APREMILAST

The present invention provides a method of chiral resolution of racemic amines of the benzyl type by means of salts formed with tartaric acid of formula (3) and intermediate of formula (2), and their use in the synthesis of Apremilast of formula 1.

ASYMMETRIC SYNTHETIC PROCESSES FOR THE PREPARATION OF AMINOSULFONE COMPOUNDS

Processes for synthesizing aminosulfone compounds are provided. Aminosulfone compounds obtained using methods provided herein are useful in production or synthesis of sulfone group containing isoindoline based compounds.

PROCESSES FOR THE PREPARATION OF (S)-1-(3-ETHOXY-4-METHOXYPHENYL)-2-METHANESULFONYLETHYLAMINE

Provided herein are new processes for the preparation of aminosulfone intermediates for the synthesis of 2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, which is useful for preventing or treating diseases or conditions related to an abnormally high level or activity of TNF-α. Further provided herein are processes for the commercial production of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine.

THIOPHENE DERIVATIVES

Disclosed is a compound of formula (1), wherein R1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the present application.

Discovery of (S)-N-{2-[1-(3-ethoxy-4-methoxy-phenyl)-2- methanesulfonylethyl]-1,3-dioxo-2,3-dihydro-1 H-isoindol-4-yl}acetamide (Apremilast), a potent and orally active phosphodiesterase 4 and tumor necrosis factor-a inhibitor

In this communication, we report the discovery of 1S (apremilast), a novel potent and orally active phosphodiesterase 4 (PDE4) and tumor necrosis factor-α inhibitor. The optimization of previously reported 3-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-(3,4-dimethoxyphenyl)propionic acid PDE4 inhibitors led to this series of sulfone analogues. Evaluation of the structure-activity relationship of substitutions on the phthalimide group led to the discovery of an acetylamino analogue 1S, which is currently in clinical trials.