223673-35-6

Basic information

• Product Name: (N-tert-Butoxycarbonyl-N-[(1'R)-hydroxy-1-phenyl)ethyl])-4-nitrophenylethylaMine
• Synonyms: (N-tert-Butoxycarbonyl-N-[(1'R)-hydroxy-1-phenyl)ethyl])-4-nitrophenylethylaMine;[(2R)-2-Hydroxy-2-phenylethyl][2-(4-nitrophenyl)ethyl]carbaMic Acid 1,1-DiMethylethyl Ester;(R)-tert-Butyl (2-hydroxy-2-phenylethyl)(4-nitrophenethyl)carbamate;MiraBegron impurity B
• CAS NO: 223673-35-6
• Molecular Formula: C21H26N2O5
• Molecular Weight: 386.44154
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 223673-35-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• Solubility: Chloroform
• CAS DataBase Reference: (N-tert-Butoxycarbonyl-N-[(1'R)-hydroxy-1-phenyl)ethyl])-4-nitrophenylethylaMine(CAS DataBase Reference)
• NIST Chemistry Reference: (N-tert-Butoxycarbonyl-N-[(1'R)-hydroxy-1-phenyl)ethyl])-4-nitrophenylethylaMine(223673-35-6)
• EPA Substance Registry System: (N-tert-Butoxycarbonyl-N-[(1'R)-hydroxy-1-phenyl)ethyl])-4-nitrophenylethylaMine(223673-35-6)

Safety Data

• Hazardous Substances Data: 223673-35-6(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Semi-Solid

Uses

Mirabegron intermediate.

Upstream product

• 223673-34-5 (R)-2-(4-nitrophenylethylamino)-1-phenylethan-1-ol hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 
• 611-71-2 (R)-Mandelic Acid 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 
• 521284-21-9 (R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride 

Relevant articles and documents

Systematic Investigation into the Formation of Significant Amounts of Unknown Impurity during Scale-up of NaBH4-I2 Mediated Reduction of Nitro-Amide Intermediate of Mirabegron No.

After successful development of a manufacturing process for the Mirabegron (1) at the laboratory scale, a muddled situation was aroused during the scale-up batches, wherein sodium borohydride-iodine (NaBH4-I2) mediated reduction of nitro-amide 4 ended up with substantial amounts (～10%) of unspecified impurity in the nitro-amine intermediate 5. On the basis of the structure elucidation and meticulous investigation, a reaction path for its genesis during the process was identified and an efficient mechanism proposed to arrest its formation. In-situ generated nickel boride (Ni2B) due to reaction of NiI2 (corrosion product) with NaBH4 followed by electrophilic attack of THF (solvent) was found to be the reason for the formation of impurity (8a). Execution of subsequent batches with proper controls arrested this impurity and successfully provided the Mirabegron with the desired quality.

Aryl or heteroaryl substituted pyrrolidine amide derivatives and application thereof

The invention discloses aryl or heteroaryl substituted pyrrolidine amide derivatives and an application thereof, in particular to a novel aryl or heteroaryl substituted pyrrolidine amide derivative and a pharmaceutical composition containing the same, which can be used for activating beta3-adrenergic receptor. The invention also relates to a method for preparing the compounds and pharmaceutical compositions, as well as an application thereof in preparing drugs for treating diseases or symptoms mediated by beta3-adrenergic receptor, and especially for treating the overactive bladder.

Acyl-substituted pyrrolidine amide derivative and application thereof

The invention discloses an acyl-substituted pyrrolidine amide derivative and application thereof. Specifically, the invention relates to a novel acyl-substituted pyrrolidine amide derivative and a pharmaceutical composition containing the compound, which can be used for activation of beta3-adrenoceptor. The invention also relates to a method for preparing the compound and the pharmaceutical composition and their application in the preparation of beta3-adrenoceptor activation-mediated diseases or symptoms, especially overactive bladder.