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

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

Used in Pharmaceutical Industry:
Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)is used as an intermediate in the synthesis of Mirabegron-related compounds. Mirabegron is a potent bladder relaxant and a reagent for diabetes remedy. Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)plays a crucial role in the development of new drugs targeting bladder control and blood sugar regulation.
Used in Chemical Synthesis:
In the chemical industry, Benzenemethanol, a-[[[2-(4-aminophenyl)ethyl]amino]methyl]-, (aR)can be used as a building block for the synthesis of various complex organic molecules. Its unique structure and functional groups make it a valuable component in the creation of new compounds with potential applications in various fields, such as materials science, agrochemistry, and pharmaceuticals.

Upstream product

• 13472-00-9 p-Aminophenethylamine 
• 20780-53-4 (R)-Styrene oxide 
• 20780-54-5 (S)-styrene oxide 
• 521284-21-9 (R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 3544-25-0 p-aminophenylacetonitrile 
• 40434-87-5 (R)-2-hydroxy-2-phenylethyl 4-methylbenzenesulfonate 
• 555-21-5 4-Nitrophenylacetonitrile 
• 223673-61-8 (R)-2-(2-aminothiazol-4-yl)-4'-[2-[(2-hydroxy-2-phenylethyl)amino]ethyl]acetanilide 
• 1460-05-5 p-nitrophenylacetaldehyde 
• 81865-10-3 2-(4-aminophenyl)ethyl chloride 
• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 

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.

Synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol

The invention discloses a synthesis method of (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol, which comprises the following processing steps: S1, adding R-2 (aminomethyl) benzyl alcohol, 4-(2-chloroethyl) aniline and triethylamine into a solvent at room temperature, and mixing; S2, after heating to 60-65 DEG C, stirring and refluxing for 1-48h; S3, pumping an obtained reaction liquid into water while the reaction liquid is hot; cooling and filtering to obtain a white solid (1R)-2-[[[2-(4-aminophenyl) ethyl] amino] methyl] benzyl alcohol; wherein the molar ratio of R-2 (aminomethyl) benzyl alcohol to 4-(2-chloroethyl) aniline in the step S1 is 1: (1-20), the solubility of 4-(2-chloroethyl) aniline in the solvent in the step S1 is 40%-60%, and the use amount of 4-(2-chloroethyl) aniline is 1-1.5 times of the mass amount of R-2 (aminomethyl) benzyl alcohol. The method has the advantages of mild reaction, simple operation, and green and environment-friendly reaction process; no irritant organic solvent is adopted; dangerous borane dimethyl sulfide is not adopted; high temperature and high pressure are not adopted; and clean production is realized.

A method for preparing milamila beilong

The invention discloses a method for preparing milamila beilong, relates to the technical field of pharmaceutical, comprising the following steps: R - mandelic acid and P ethylamine under high-temperature to amide condensation reaction, to obtain the intermediate (R)- 2 - hydroxy - N - (4 - nitrophenyl ethyl) - 2 - phenyl acetamide; then diisobutyl hydrogenated aluminum reducing amide carbonyl, to obtain the intermediate (R)- 2 - ((4 - nitrophenyl ethyl) amino) - 1 - phenyl ethanol hydrochloride; ammonium formate - Pd/C by nitro reduction system, to obtain the intermediate (R)- 2 - ((4 - amino ethyl) amino) - 1 - phenyl ethanol; finally with the amino thiazole acetic acid to generate a condensation reaction, to obtain milamila beilong. The invention prepared milamila beilong purity is good, high yield, synthetic line few steps, conditions is mild and controllable, the operation is simple, low cost, and is suitable for industrial production, and with extensive prospect and industrial application value.

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.

Targeting a Mirabegron precursor by BH3-mediated continuous flow reduction process

A continuous-flow reduction of (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide, involved in the synthetic pathway of Mirabegron, has been developed. This study demonstrated the possibility to safely handling BH3 complexes within microfluidic reactors using 2-MeTHF as greener alternative to traditional solvents, and without requiring any additive such as DMI. In addition, NMR and HPLC purity analysis revealed that the sole by-product of this process is the diamine 3, which wouldn't affect the following synthetic steps towards Mirabegron.

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.

Synthetic method of the compound

A synthesis method of a compound shown as a formula 1 is provided. The method includes (1) bringing a compound shown as a formula 2 into contact with compound shown as a formula 3 to produce a compound shown as a formula 4; (2) subjecting nitro of the compound shown as the formula 4 to a reduction reaction to produce a compound shown as a formula 5; and (3) bringing the compound shown as the formula 5 into contact with a compound shown as a formula 6 to produce the compound shown as the formula 1. The method is short in route. Initial raw materials are cheap and easily available. All the intermediates are easy to purify and simple in after-treatment. The product is high in purity and high in yield. The method benefits industrial production.

Diamine-Tethered Bis(thiourea) Organocatalyst for Asymmetric Henry Reaction

We have developed a novel multifunctional C2-symmetric biphenyl-based diamine-tethered bis(thiourea) organocatalyst, which was tested in the asymmetric Henry reaction. Under thoroughly optimized conditions, the catalyst provided exceptionally high yields and excellent enantioselectivities especially for electron-deficient aromatic and heterocyclic substrates. Due to a high affinity of the catalyst to silica gel, a simple chromatography-free nitroaldol isolation procedure was feasible. Preliminary kinetic and spectroscopic experiments were performed in order to complete the mechanistic picture of the organocatalyzed nitroaldolization process. Finally, the developed synthetic strategy was successfully applied to the catalytic enantioselective syntheses of enantiopure (S)-econazole and (R)-mirabegron a late-stage intermediate.

METHOD FOR THE PRODUCTION OF MORPHOLOGICALLY HOMOGENOUS MIRABEGRON AND MIRABEGRON MONOHYDROCHLORIDE

The object of the present invention relates to a method for the production of formula 1 (R)-2- (2-aminothiazole-4-yl)-4'-[2-[(2-hydroxy-2-phenyl)ethylamino]ethyl]acetanilide (mirabegron) and formula 1c mirabegron monohydrochloride, as well as the intermed

Study on a New Method for Synthesis of Mirabegron

Mirabegron is a muscle relaxing drug for the treatment of overactive bladder. The existing synthetic methods for mirabegron produced intermediate product 4-(2-(phenethylamino)ethyl)aniline, which complicated the final product purification process. In this study, we designed a new synthetic route for mirabegron with low cost starting materials and a production of mirabegron at a 99.6% purity and a 61% overall yield. Particularly, this new synthetic route did not produce side product 4-(2-(phenethylamino)ethyl)aniline, which significantly simplified the product purification process.