104338-26-3

Usage

Uses

Used in Pharmaceutical Industry:
[2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE is used as an intermediate in the synthesis of various drugs, including antihistamines and antidepressants, for its ability to contribute to the development of medications that address allergic reactions and mood disorders.
Used in Organic Synthesis:
In the field of organic synthesis, [2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE is utilized as a reagent or building block, enabling the creation of a wide range of organic compounds for various applications, from pharmaceuticals to specialty chemicals.
Used in Chemical Research:
[2-(2-METHOXYPHENYL)ETHYL](METHYL)AMINE is also employed in chemical research as a component in experiments and studies aimed at understanding its properties and potential applications in new chemical reactions or processes.

Upstream product

• 2045-79-6 o-methoxy-2-phenylethylamine 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 131699-15-5 N-(t-Butyloxycarbonyl)-2-(2-methoxyphenyl)-ethylamine 
• 258882-54-1 N-(methoxycarbonyl)-2-(2-methoxyphenyl)ethylamine 
• 59734-18-8 3-(2-methoxy-phenyl)-propionic acid amide 
• 6342-77-4 2-methoxy-benzenepropanoic acid 

Downstream Products

• 69226-64-8 N-(2-methoxy-phenethyl)-N-methyl-urea 
• 154585-18-9 2-(2-methylamino-ethyl)-phenol 
• 1282042-14-1 C₂₀H₂₂N₄O₂ 

Relevant academic research and scientific papers

Palladium-Catalyzed C(sp2)-H Olefination of Free Primary and Secondary 2-Phenylethylamines: Access to Tetrahydroisoquinolines

A rapid construction of THIQs by a Pd(II)-catalyzed C(sp2)-H olefination of free primary and secondary 2-phenylethylamines with high step- and atom-economy was reported. Notably, no substituent was required at the α-position to the amino group of the 2-phenylethylamines. The substrate scope was broad, and the reaction could also be applied to generate THIQs from the biologically active molecules such as the drug molecule baclofen and phenylalanine ester.

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

Iron-Catalyzed Intramolecular C—H Amidation of N-Benzoyloxyureas

A redox-neutral Fe-catalyzed intramolecular C—H amidation of N-benzoyloxyureas is described. This methodology employs a simple iron complex in situ generated from Fe(OTf)2 and bipyridine as the catalyst and N-benzoyloxyureas as the nitrene prec

INHIBITORS OF N-ACYLPHOSPHATIDYLETHANOLAMINE PHOSPHOLIPASE D (NAPE-PLD)

The invention relates to a compound of the formula (I) as novel inhibitor of N-acylphosphatidylethanolamine phospholipase D (NAPE-PLD), and to use thereof for the prophylaxis or treatment of diseases associated with NAPE-PLD. wherein in a ring A, X1 is N, or CR4; X2 is N or CR5; X3 is N or CH; with the proviso that at least one of X1 and X3 is N.

Selective N-methylation of primary aliphatic amines with dimethyl carbonate in the presence of alkali cation exchanged Y-faujasites

The N-methylation of aliphatic amines [XC6H4(CH 2)nNH2; n=1, X=H (1a), o-MeO (1b), p-MeO (1c); n=2, X=H (2a), o-MeO (2b); 1d: PhCH(Me)NH2] with dimethyl carbonate (DMC) is efficiently catalysed by NaY faujasite: on condition that CO 2 (a co-product of the reaction) is carefully removed, N-methyl- and N,N-dimethyl-amines (RNHMe and RNMe2) are obtained in good overall yields (70-90%). Otherwise, in the presence of CO2, carbamates (RNHCO2Me) form competitively to a large extent. The reaction probably proceeds through a BAl2 displacement of the amine on DMC.