51484-40-3

Basic information

• Product Name: N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide
• Synonyms: N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide;difenpiramide;Difenpyramide;N-(2-Pyridinyl)-1,1'-biphenyl-4-acetamide;2-(4-phenylphenyl)-N-pyridin-2-ylacetamide
• CAS NO: 51484-40-3
• Molecular Formula: C₁₉H₁₆N₂O
• Molecular Weight: 288.34314
• EINECS: 257-235-9
• Mol File: 51484-40-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 122-124°
• Boiling Point: 549°Cat760mmHg
• Flash Point: 285.8°C
• Appearance: /
• Density: 1.192g/cm³
• CAS DataBase Reference: N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide(51484-40-3)
• EPA Substance Registry System: N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide(51484-40-3)

Safety Data

• Hazardous Substances Data: 51484-40-3(Hazardous Substances Data)

Usage

Description

N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide is a monocarboxylic acid amide that is formed through the formal condensation of the carboxy group from biphenyl-4-ylacetic acid with the amino group of 2-aminopyridine. N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide has been identified for its potential therapeutic applications, particularly in the treatment of rheumatoid arthritis.

Uses

Used in Pharmaceutical Industry:
N-pyridin-2-yl[1,1'-biphenyl]-4-acetamide is used as a therapeutic agent for the treatment of rheumatoid arthritis. Its application is based on its ability to modulate the immune system and reduce inflammation, which are key factors in the pathology of rheumatoid arthritis.

Originator

Difenax,Zambeletti,Italy,1977

Manufacturing Process

23 g (0.1 mol) diphenylacetic acid chloride dissolved in 300 cc anhydrous ethyl ether are slowly added dropwise to a solution of 19 g (0.2 mol) 2- aminopyridine in 300 cc anhydrous ethyl ether. The reaction mixture is agitated and the temperature is kept at between 5°C and 10°C with an ice bath. After the addition has been completed, the agitation of the mixture is continued and the temperature is allowed to rise to 20°C to 25°C. After leaving to stand for a few hours, the gummy precipitate solidifies and becomes filterable. After separating off the precipitate, the ether is evaporated under reduced pressure to a volume of about 100 cc.The ether is left to stand at a low temperature below 10°C when the remaining portion of the product precipitates and is filtered off and added to the first precipitate. The product thus obtained is thoroughly washed, first in water and then in a solution of sodium bicarbonate, and then again in water. After drying in air, the product is crystallized from anhydrous ethanol or from acetone and water. The analytical data correspond to calculated values. Yield is 18 g; MP 122°C to 124°C.

Therapeutic Function

Antiinflammatory

Upstream product

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Relevant articles and documents

Ruthenium-Catalyzed Reductive Arylation of N-(2-Pyridinyl)amides with Isopropanol and Arylboronate Esters

A new three-component reductive arylation of amides with stable reactants (iPrOH and arylboronate esters), making use of a 2-pyridinyl (Py) directing group, is described. The N-Py-amide substrates are readily prepared from carboxylic acids and PyNH2, and the resulting N-Py-1-arylalkanamine reaction products are easily transformed into the corresponding chlorides by substitution of the HN-Py group with HCl. The 1-aryl-1-chloroalkane products allow substitution and cross-coupling reactions. Therefore, a general protocol for the transformation of carboxylic acids into a variety of functionalities is obtained. The Py-NH2 by-product can be recycled.

Physicochemical profile of a new antiinflammatory drug: Difenpiramide

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