861448-74-0

Usage

Chemical Properties

Off-white Solid

Uses

Reactant in the preparation of β-3 Adrenergic Receptor Agonists.

Upstream product

• 113520-36-8 2-(4-(2-ethoxy-2-oxoethyl)phenyl)acetic acid 
• 676-58-4 methylmagnesium chloride 
• 36076-25-2 (4-methoxycarbonylmethylphenyl)acetic acid methyl ester 
• 17833-56-6 ester monomethylique de l'acide p-phenylene diacetique 
• 75-16-1 methylmagnesium bromide 
• 7325-46-4 1,4-phenylenediacetic acid 
• 622-75-3 1,4-phenylenediacetonitrile 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 84541-92-4 methyl [4-(2-oxopropyl)phenyl]acetate 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 88594-72-3 [4-(2-oxopropyl)phenyl]acetic acid 

Downstream Products

• 1251957-82-0 2-[4-(2-hydroxy-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 
• 1251957-87-5 2-[4-(2-{[(2R)-2-hydroxy-2-(pyridin-3-yl)ethyl]amino}-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 
• 1251957-71-7 2-[4-(2-{[(2S)-2-hydroxy-2-(pyridin-2-yl)ethyl]amino}-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 
• 1251957-83-1 2-chloro-N-[1,1-dimethyl-2-(4-{2-[(5-methylisoxazol-3-yl)amino]-2-oxoethyl}phenyl)ethyl]acetamide 
• 1251957-84-2 2-[4-(2-amino-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 
• 1251957-86-4 2-[4-(2-{[(2R)-2-(6-chloropyridin-3-yl)-2-hydroxyethyl]amino}-2-methylpropyl)phenyl]-N-(5-methylisoxazol-3-yl)acetamide 

Relevant academic research and scientific papers

Application of biocatalysis towards asymmetric reduction and hydrolytic desymmetrisation in the synthesis of a β-3 receptor agonist

Chemoenzymatic syntheses of two key intermediates in the preparation of a potent β-3 receptor agonist 1 are described. A lipase-catalysed hydrolytic desymmetrisation is employed in a new synthesis of intermediate 7, which avoids the use of alkyl-tin reagents. A second biotransformation delivers chiral chlorohydrin 5 from its parent ketone in greater enantiomeric excess than the previously-described Noyori-reduction process. A brief discussion of the enantioselectivity of a set of single-point mutants of Sporobolomyces salmonicolor aldehyde reductase in this bioreduction is also presented.

The synthesis of two potent β-3 adrenergic receptor agonists

This contribution describes the initial preparation of two potent β-3 receptor agonists 1 and 2. Subsequent scale up of these two compounds was required for further evaluation and proceeded via a common key amine intermediate 24. Synthesis of this key intermediate by way of a Ritter reaction was a vital step in the sequence. Enantioselective Noyori hydrogenation reactions gave access to the chiral epoxides necessary to make the target compounds. Chemistry was developed for the selective dehalogenation of the 2-chloropyridyl group in the presence of a sensitive isoxazole unit to provide access to 1.

Sulfonamide derivatives for the treatment of diseases

The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.