223673-34-5

Usage

Uses

Used in Pharmaceutical Industry:
(alphaR)-alpha-[[[2-(4-Nitrophenyl)ethyl]amino]methyl]benzenemethanol is used as a potential pharmaceutical compound for its complex structure and reactivity, which may contribute to the development of new drugs. Its specific properties and interactions with biological systems need to be further explored to understand its full potential in medicinal chemistry.
Used in Organic Synthesis:
In the field of organic synthesis, (alphaR)-alpha-[[[2-(4-Nitrophenyl)ethyl]amino]methyl]benzenemethanol can be utilized as a building block or intermediate in the synthesis of more complex organic molecules. Its unique structural features may facilitate the creation of novel compounds with specific functions or properties.

Upstream product

• 20780-53-4 (R)-Styrene oxide 
• 24954-67-4 2-(p-nitrophenyl)ethylamine 
• 521284-19-5 (2R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylethanamide 
• 29968-78-3 2-(4-nitrophenyl)ethylamine monohydrochloride 
• 555-21-5 4-Nitrophenylacetonitrile 
• 1460-05-5 p-nitrophenylacetaldehyde 
• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 611-71-2 (R)-Mandelic Acid 
• 70-11-1 α-bromoacetophenone 

Downstream Products

• 521284-21-9 (R)-2-[[2′-(4-nitrophenyl)ethyl]amino]-1-phenylethanol hydrochloride 

Relevant academic research and scientific papers

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.

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.

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.

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.

Nitrogen heterocyclic ring group substituted amide derivative and application thereof

The invention discloses a nitrogen heterocyclic ring group substituted amide derivative and application thereof, particularly relates to a novel nitrogen heterocyclic ring group substituted amide derivative and a drug composition comprising the compound, and further relates to methods for preparing the compound and the drug composition, and application of the compound and the drug composition to preparation of drugs for treating diseases or symptoms, particularly overactive bladder, excited and mediated by beta 3-adrenergic receptors. The compound and the drug composition can be used for activating the beta 3-adrenergic receptors.

Amide substituted pyrrolidine amide derivatives and use thereof (by machine translation)

The invention discloses amide substituted pyrrolidine amide derivatives and their use, in particular, the invention relates to a novel class of amide substituted pyrrolidine amide derivatives containing such compounds and pharmaceutical composition, can be used to activate β 3 - adrenergic receptor. The invention also relates to processes for preparing such compounds and pharmaceutical compositions, and in the preparation of the treatment by the β 3 - adrenergic receptor activation mediated diseases or conditions, in particular the overactive bladder of the use of the medicament. (by machine translation)

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.

Synthesis of mirabegron intermediate (R)-2-(4-nitrophenethylamino)-1-phenylethanol hydrochloride

The invention discloses synthesis of a mirabegron intermediate (R)-2-(4-nitrophenethylamino)-1-phenylethanol hydrochloride. The synthesis comprises the following steps: firstly, enabling alpha-bromoacetophenone and 4-nitro-phenethylamine to react in a solvent in the presence of alkali to generate an intermediate I; then carrying out reduction reaction on the intermediate I under the action of a chiral inducing agent and a reducing agent to generate an intermediate II; enabling the intermediate II to react with concentrated hydrochloric acid in a solvent to generate a target product. Accordingto the synthesis method disclosed by the invention, EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide), HOBt (Hydroxybenzotriazole) and DMI (1,3-dimethyl-2-imidazolidinone) which have a relatively high price, and hypertoxic R-styrene oxide can be avoided; the synthesis method has the advantages of easiness for obtaining raw materials, low cost, simplicity in operation and few impurities and is suitable for industrial production.

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.

Mirabegron intermediate post-treatment method

The invention relates to a mirabegron intermediate II post-treatment method. The post-treatment method comprises the following steps that a mirabegron carbonyl compound shown in a formula I is used as a raw reaction material, and amide is reduced under the effect of a borane reagent through reduction reaction; after complete reaction, and cooling and quenching reaction are performed to obtain a mixture; reduced pressure distillation and cooling are performed, and water and an organic solvent are added to the mixture; a pH value is regulated by using strong unitary base, stirring is performed till a water layer and an organic layer are clarified, and standing is performed for layering; organic phases are separated for standby application; the formula I and a structural formula I are shown in the description. The raw materials and reagents required by the borane reagent reaction system post-treatment method are cheap and have a very good economic effect, especially the strong unitary base is adopted to replace carbonate for mirabegron nitro compound post-treatment, the base consumption and water consumption for treatment can be reduced, accordingly three wastes are decreased, meanwhile inorganic salt undissolved substances are avoided by controlling the solution pH, and the mirabegron intermediate II post-treatment method is suitable for industrial production.