39496-45-2

Usage

Preparation

To a 50-ml pear-shaped flask equipped with a water-reflux condenser, a gas inlet tube reaching the bottom of the flask, and a gas outlet tube fitted with a drying tube is added 2.85 ml (2.90 g, 24.7 mmol) of phenylacetonit-rile, 1.00 ml of dry methanol (0.80 g, 24.7 mmol) and 7 ml of anhydrous ether. The flask is cooled in an ice bath while dry hydrogen chloride gas (first passed through sulfuric acid) is passed into the solution until no more was absorbed.The flask is then disconnected, stoppered tightly, and stored at -10°C overnight. A solid forms, which is isolated by filtration under a stream of argon gas and then dried under reduced pressure for 4 hrs, to yield 4.30 g (23.2 mmol or 94% yield) of a white free-flowing powder. The NMR (CDCI3, 90MHz) indicated 7.32 (m, 5H), 4.23 (s, 3H), 4.05 (s, 2H).

InChI:InChI=1/C9H11NO/c1-11-9(10)7-8-5-3-2-4-6-8/h2-6,10H,7H2,1H3/b10-9-

Upstream product

• 67-56-1 methanol 
• 140-29-4 phenylacetonitrile 

Downstream Products

• 4369-00-0 (2,2,2-trimethoxyethyl)benzene 
• 621-72-7 2-benzylbenzimidazole 
• 77570-24-2 5-(1-Amino-2-phenyl-ethylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 104303-67-5 5-[1-Benzo[1,3]dioxol-5-yl-meth-(Z)-ylidene]-2-benzyl-3,5-dihydro-imidazol-4-one 
• 51688-21-2 C₁₀H₁₀N₂O 
• 143780-57-8 C₁₆H₁₇N₃ 
• 157160-61-7 (S)-2-benzyl-2-oxazoline-4-carboxylic acid methyl ester 
• 33675-12-6 2-benzyl-5-(4-methoxy-benzylidene)-3,5-dihydro-imidazol-4-one 
• 139688-90-7 4,5-Dihydro-1,3-dimethyl-2-(phenylmethyl)imidazolium-hexafluorophosphat 
• 4765-56-4 glycosminine 

Relevant academic research and scientific papers

D-Amino acid oxidase inhibitors based on the 5-hydroxy-1,2,4-triazin-6(1H)-one scaffold

A series of 3-substituted 5-hydroxy-1,2,4-triazin-6(1H)-one derivatives were designed and synthesized as a new class of d-amino acid oxidase (DAAO) inhibitors. Some of the newly synthesized derivatives showed potent inhibitory activity against human DAAO with IC50 values in the nanomolar range. Among them, 6-hydroxy-3-phenethyl-1,2,4-triazin-5(2H)-one 6b and 3-((6-fluoronaphthalen-2-yl)methylthio)-6-hydroxy-1,2,4-triazin-5(2H)-one 6m were found to be metabolically stable in mouse liver microsomes. In addition, compound 6b was found to be orally available in mice and able to enhance plasma d-serine levels following its co-administration with d-serine compared to the oral administration of d-serine alone.

PARTICLES, COMPOSITIONS, AND METHODS FOR OPHTHALMIC AND/OR OTHER APPLICATIONS

This disclosure relates to particles, compositions, and methods that aid particle transport in mucus are provided. The particles, compositions, and methods may be used, in some instances, for ophthalmic and/or other applications.

Copper(II)-Mediated Aerobic Oxidation of Benzylimidates: Synthesis of Primary α-Ketoamides

A simple and straightforward method for the synthesis of primary α-ketoamides has been discovered. The reaction represents the first example of benzylimidates directly converting to primary α-ketoamides by using sustainable molecular oxygen as an oxidant. This reaction proceeds in the presence of copper(II) salt via cleavage of benzylic C-H and C-O bonds of the benzylimidates with liberation of alcohols as the only byproduct. A wide substrate scope, operationally mild conditions, the use of single substrates, and a reaction scaled up to grams make this strategy very attractive and practical. Furthermore, mechanistic studies illustrate that the imidate group adjacent to the benzylic position plays crucial role in facilitating this chemical process.

Copper(II)-Catalyzed Benzylic C(sp3)-H Aerobic Oxidation of (Hetero)Aryl Acetimidates: Synthesis of Aryl-α-ketoesters

A straightforward method is developed in this paper for the synthesis of α-ketoesters through copper-catalyzed aerobic oxidation of (hetero)aryl acetimidates using molecular oxygen as a sustainable oxidant. The reaction represents the first example of the direct synthesis of aryl-α-ketoesters from arylacetimidates through the aerobic oxidation of a benzylic C(sp3)-H (CO) bond in moderate to good yield. This transformation occurs under mild reaction conditions with a wide range of substrates and utilizes a readily available oxidant and catalyst. The synthetic utility of this transformation is demonstrated through scaled-up synthesis. A plausible reaction mechanism is also proposed.

Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration

The preparation and resolution of a series of axially chiral quinazoline-containing ligands is described in which the key steps are the metal-catalyzed naphthyl-phosphorus bond formation, the naphthalene-quinazoline Suzuki coupling, and the preparation of the Suzuki electrophilic components from the corresponding imidate and anthranilic acid. Diastereomeric palladacycles derived from the racemic phosphinamines and (+)-di-μ-chlorobis[(R)- dimethyl(1-(1-naphthyl)ethyl)-aminato-C2,N]dipalladium(II) were separated by fractional crystallization. The configuration of the resulting diastereomers was determined by X-ray crystallographic analysis. Displacement of the resolving agent by reaction with 1,2-bis(diphenylphosphino)ethane afforded enantiopure ligand in each case. Their rhodium complexes were prepared and applied in the enantioselective hydroboration of a range of vinylarenes. The quinazolinap catalysts were found to be extremely active, giving excellent conversions, good to complete regioselectivities, and the highest enantioselectivities obtained to date for several members of the vinylarene class, including cis-β-methylstyrene (97%), cis-stilbene (99%), and indene (99.5%).

Synthesis and biological evaluation of trehalose analogs as potential inhibitors of mycobacterial cell wall biosynthesis

Analogs of trehalose are reported that were designed to interfere with mycolylation pathways in the mycobacterial cell wall. Several derivatives of 6,6′-dideoxytrehalose, including N,N′-dialkylamino and 6,6′-bis(sulfonamido) analogs, were prepared and evaluated for antimycobacterial activity against Mycobacterium tuberculosis H37Ra and a panel of clinical isolates of Mycobacterium avium. 6,6′-Diaminotrehalose and its diazido precursor were both inactive, but significant activity apparently related to aliphatic chain length was found among the sulfonamides, N-alkylamines, and one of the amidines.

A facile and versatile route to 2-substituted-4(3H)-quinazolinones and quinazolines

A range of 2-aryl and 2-alkyl quinazolinones have been prepared in moderate to good yields from the reaction of anthranilic acid and the appropriately substituted imidate in a facile, mild, onepot procedure. Subsequent reaction with phosphorus oxychloride afforded the corresponding 4-chloro-2-substituted quinazolines, which are useful synthetic intermediates, in good to high yields. Product isolation was facilitated by the development of work up procedures for both reactions that did not include purification by column chromatography.

Synthesis of N-(α-Methoxyalkyl) Amides from Imidates

Two general routes from imidates to N-(α-methoxyalkyl) amides (e.g.,R'CONHCH(OCH3)R, 1) are reported.The first involves acylation of the imidate on nitrogen with an acyl chloride, followed by reduction with sodium borohydride.In the second, an aldehyde is converted, via its methyl acetal, to an α-chloro methyl ether, which is used to alkylate the imdate.Further treatment with pyridinium chloride in dry Me2SO yields 1.Thirteen examples are reported.