391901-45-4

Basic information

• Product Name: BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-
• Synonyms: BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-;BenzeneMethanol, -[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (R)-;(alphaR)-alpha-[[[2-(4-Aminophenyl)ethyl]amino]methyl]-benzenemethanol;(R)-2-((4-AMinophenethyl)aMino)-1-phenylethanol;Mirabegron Impurity 20;(R)-2-((4-aminophenethyl)amino)-1-phenylethan-1-ol;(1 R)-2-[(4-aminophenethyl)amino]-1-phenyl-1-ethanol;MiraBegron impurity H
• CAS NO: 391901-45-4
• Molecular Formula: C₁₆H₂₀N₂O
• Molecular Weight: 256.3428
• Product Categories: CMLLYL
• Mol File: 391901-45-4.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 447.9±24.0 °C(Predicted)
• Appearance: /
• Density: 1.137±0.06 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), DMSO (Sparingly), Methanol (Slightly)
• PKA: 13.98±0.20(Predicted)
• CAS DataBase Reference: BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-(391901-45-4)
• EPA Substance Registry System: BenzeneMethanol, a-[[[2-(4-aMinophenyl)ethyl]aMino]Methyl]-, (aR)-(391901-45-4)

Safety Data

• Hazardous Substances Data: 391901-45-4(Hazardous Substances Data)

Usage

Uses

(R)-2-((4-Aminophenethyl)amino)-1-phenylethanol is an intermediate in the synthesis of Mirabegron related compounds. irabegron is a potent bladder relaxant and reagent for diabetes remedy.

Upstream product

• 611-71-2 (R)-Mandelic Acid 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 
• 223673-61-8 (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide 
• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 4561-43-7 2-amino-1-phenylethanol hydrochloride 
• 141377-54-0 2-nitro-1-phenylethan-1-ol 
• 18867-43-1 (R)-2-amino-1-phenyl-ethanol; hydrochloride 
• 96-09-3 styrene oxide 
• 211635-75-5 N-benzyl-N-[2-(4-nitrophenyl)ethyl]amine 
• 555-21-5 4-Nitrophenylacetonitrile 
• 13472-00-9 p-Aminophenethylamine 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 3544-25-0 p-aminophenylacetonitrile 

Downstream Products

• 223673-61-8 (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide 
• 391901-46-5 tert-butyl 4-[(2,4-dioxo-1,3-thiazolidin-5-yl)amino]phenethyl[(2 R)-2-hydroxy-2-phenylethyl]carbamate 
• 223673-36-7 (R)-(4-aminophenylethyl)(2-hydroxy-2-phenylethyl)carbamic acid tert-butyl ester 

Relevant articles and documents

Preparation method of mirabegron key intermediate

The invention provides a preparation method of a mirabegron key intermediate, namely, a compound as shown in a formula (III). The method is simple, convenient and safe to operate, free of harsh reaction conditions, high in reaction purity and yield and low in process cost which is about 40% of that of a process using a metal catalyst such as palladium carbon, is suitable for large-scale production and conforms to the green chemistry principle. A finished product of mirabegron continues to be prepared by using the intermediate compound as shown in the formula (III) prepared by the method so as to meet the existing requirements.

Preparation method of mirabegron

The invention discloses a preparation method of mirabegron, and the method comprises: S1, carrying out reduction reaction on p-nitrophenylacetonitrile to obtain p-nitrophenylacetaldehyde; S2, carryingout condensation reduction on the p-nitrophenylacetaldehyde and (R) 2-amino-1-phenethyl alcohol to obtain (R) 2-(4-nitrophenethyl) amino)-1-phenyl ethyl alcohol; S3, carrying out reduction on the (R)2-amino-1-phenethyl alcohol to obtain (R) 2-(4-nitrophenethyl) amino)-1-phenyl ethyl alcohol to obtain an intermediate (R) 2-((4-aminophenyl ethyl) amino)-1-phenyl ethyl alcohol; and S4, carrying outcondensation on the (R) 2-((4-aminophenyl ethyl) amino)-1-phenyl ethyl alcohol and aminothiazole acetic acid to obtain the mirabegron. According to the method, the starting raw materials are cheap and easy to obtain, the reaction conditions are controllable, the synthetic route steps are few, the yield is high, the cost is low, and the prepared mirabegron is high in purity.

Identification of Uridine 5′-Diphosphate-Glucuronosyltransferases Responsible for the Glucuronidation of Mirabegron, a Potent and Selective β3-Adrenoceptor Agonist, in Human Liver Microsomes

Background and Objectives: Mirabegron is cleared by multiple mechanisms, including drug-metabolizing enzymes. One of the most important clearance pathways is direct glucuronidation. In humans, M11 (O-glucuronide), M13 (carbamoyl-glucuronide), and M14 (N-glucuronide) have been identified, of which M11 is one of the major metabolites in human plasma. The objective of this study was to identify the uridine 5′-diphosphate (UDP)-glucuronosyltransferase (UGT) isoform responsible for the direct glucuronidation of mirabegron using human liver microsomes (HLMs) and recombinant human UGTs (rhUGTs). Methods: Reaction mixtures contained 1–1000?μM mirabegron, 8?mM MgCl2, alamethicin (25?μg/mL), 50?mM Tris–HCl buffer (pH 7.5), human liver microsome?(HLM) or rhUGT (1.0?mg protein/mL), and 2?mM UDP-glucuronic acid in a total volume of 200?μL for 120?min at 37?°C. HLMs from 16 individuals were used for the correlation study, and mefenamic acid and propofol were used for the inhibition study. Results: Regarding M11 formation, rhUGT2B7 showed high activity among the rhUGTs tested (11.3?pmol/min/mg protein). This result was supported by the correlation between M11 formation activity and UGT2B7 marker enzyme activity (3-glucuronidation of morphine, r2?=?0.330, p?=?0.020) in individual HLMs; inhibition by mefenamic acid in pooled HLMs (IC50?=?22.8?μM); and relatively similar Km values between pooled HLMs and rhUGT2B7 (1260 vs. 486?μM). Regarding M13 and M14 formation, rhUGT1A3 and rhUGT1A8 showed high activity among the rhUGTs tested, respectively. Conclusions: UGT2B7 is the main catalyst of M11 formation in HLMs. Regarding M13 and M14 formation, UGT1A3 and UGT1A8 are strong candidates for glucuronidation, respectively.