203321-88-4

Basic information

• Product Name: (2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide
• Synonyms: (2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide
• CAS NO: 203321-88-4
• Molecular Weight: 444.525
• Mol File: 203321-88-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide(203321-88-4)
• EPA Substance Registry System: (2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide(203321-88-4)

Safety Data

• Hazardous Substances Data: 203321-88-4(Hazardous Substances Data)

Usage

Description

(2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide is a complex organic compound with a unique structure and potential biological activity. It features a piperidine ring connected to a phenylacetamide moiety, a difluorocyclopentyl group, and a 6-aminopyridine side chain. The stereochemistry of the molecule is defined by the (2R) and (1R) descriptors, which specify the orientation of its chiral centers. This highly specific and intricately designed molecule may have applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
(2R)-N-[1-(6-Aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide is used as a pharmaceutical compound for its potential biological activity. The presence of various functional groups and substructures, such as the piperidine ring, phenylacetamide moiety, difluorocyclopentyl group, and 6-aminopyridine side chain, may contribute to its therapeutic effects. The specific stereochemistry, indicated by the (2R) and (1R) descriptors, ensures the desired orientation of chiral centers, which is crucial for the compound's efficacy and selectivity.

Upstream product

• 203321-57-7 (2R,5R)-2-(tert-butyl)-5-[(1R)-3,3-difluorocyclopentyl]-5-phenyl-1,3-dioxolan-4-one 
• 203321-55-5 (2R,5R)-2-(tert-butyl)-5-[(1R)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one 
• 303763-38-4 {1-[6-(benzhydrylidene-amino)-pyridin-2-ylmethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester 
• 372948-90-8 N-(6{[4-(acetylamino)-1-piperidinyl]methyl}-2-pyridinyl)-2,2-dimethylpropanamide 
• 372948-82-8 2-pivaloylaminopyridine-6-carboxaldehyde 
• 303763-39-5 4-(tert-butoxycarbonylamino)-1-[(6-aminopyridin-2-yl)methyl]piperidine 
• 303763-37-3 4-(tert-butoxycarbonylamino)-1-[(6-bromopyridin-2-yl)methyl]piperidine 
• 73889-19-7 tert-butyl (1-benzylpiperidin-4-yl)carbamate 
• 34160-40-2 6-bromo-2-pyridinecarbaldehyde 
• 50541-93-0 4-amino-1-benzylpiperidine 
• 626-05-1 2,6-Dibromopyridine 
• 203321-56-6 (2R)-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetic acid 

Relevant articles and documents

Thiazolidinone, oxazolidinone, and imidazolone derivatives for treating non-inflammatory gastrointestinal tract disorders

A method is provided for using Cav2.2 subunit calcium channel modulators, particularly thiazolidinone, oxazolidinone, and imidazolone derivatives, to treat non-inflammatory gastrointestinal tract disorders.

Synthesis of a muscarinic receptor antagonist via a diastereoselective Michael reaction, selective deoxyfluorination and aromatic metal-halogen exchange reaction

An efficient synthesis of a structurally unique, novel M3 antagonist 1 is described. Compound 1 is conveniently disconnected retrosynthetically at the amide bond to reveal the acid portion 2 and the amine fragment 3. The synthesis of key intermediate 2 is highlighted by a ZnCl2-MAEP complex 19 catalyzed diastereoselective Michael reaction of dioxolane 7 with 2-cyclopenten-1-one (5) to establish the contiguous quaternary-tertiary chiral centers and a subsequent geminal difluorination of ketone 17 using Deoxofluor in the presence of catalytic BF3·OEt2. The synthesis of the amine moiety 3 is highlighted by the discovery of a novel n-Bu3MgLi magnesium-halogen exchange reaction for selective functionalization of 2,6-dibromopyridine. This new and practical metalation protocol obviated cryogenic conditions and upon quenching with DMF gave 6-bromo-2-formylpyridine (26) in excellent yield. Further transformations afforded the amine fragment 3 via reductive amination with 35, Pd-catalyzed aromatic amination, and deprotection. Finally, the highly convergent synthesis of 1 was accomplished by coupling of the two fragments. This synthesis has been used to prepare multi-kilogram quantities of the bulk drug.

Fluorine-containing 1,4-disubstituted piperidine derivatives

Novel fluorine-containing 1,4-disubstituted piperidine derivatives, represented by general formula ?I! STR1 such as, for example, (2R)-N-?1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl!-2-?(1R)-3,3-difluorocyclopentyl!-2-hydroxy-2-phenylacetamide or pharmaceutically acceptable salt thereof, are potent and selective antagonists for muscarinic M3 receptors with little side effects. The compounds of formula ?I! exhibit excellent oral activity, duration of activity and pharmacolkinetics. They are useful for treatment and prophylaxis of respiratory diseases, such as chronic obstructive pulmonary diseases; urinary diseases, such as urinary incontinence; and digestive diseases, such as irritable bowel syndrome, and motion sickness.