6628-81-5

Usage

Uses

Used in Pharmaceutical Industry:
N-(1-methyl-2-oxopropyl)acetamide is utilized as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure allows it to serve as a building block in the creation of new medicinal compounds, contributing to the development of novel treatments for a range of health conditions.
Used in Neurological Disorder Treatment:
In the field of neurology, N-(1-methyl-2-oxopropyl)acetamide is studied for its potential role in treating neurological disorders. Its specific properties may offer therapeutic benefits, although further research is necessary to fully understand its mechanisms of action and efficacy.
Used as an Analgesic Agent:
N-(1-methyl-2-oxopropyl)acetamide is also considered for its analgesic properties, suggesting that it could be used to alleviate pain. N-(1-methyl-2-oxopropyl)acetamide's ability to interact with pain receptors or pathways is an area of interest for pain management therapies.
Safety Considerations:
Despite its potential benefits, N-(1-methyl-2-oxopropyl)acetamide is recognized to have low toxicity and is generally regarded as safe for use in pharmaceutical applications. However, as with any chemical compound, it is imperative to handle and use it with appropriate care and safety precautions to minimize any potential risks.

InChI:InChI=1/C6H11NO2/c1-4(5(2)8)7-6(3)9/h4H,1-3H3,(H,7,9)

Upstream product

• 108-24-7 acetic anhydride 
• 302-72-7 rac-Ala-OH 
• 135636-66-7 butane-2,3-dione mono-oxime 
• 1115-69-1 Ac-DL-Ala 
• 64-19-7 acetic acid 
• 144522-62-3 N-(2-Ethyl-4-oxo-4H-quinazolin-3-yl)-N-((Z)-2-hydroxy-1-methyl-propenyl)-acetamide 
• 64505-07-3 N-(3-oxobut-1-en-2-yl)acetamide 
• 75-36-5 acetyl chloride 
• 17292-61-4 2,3-butanedione mono-(O-acetyl oxime) 
• 13732-32-6 biacetyl phenylhydrazone 
• 110788-53-9 (1E)-2-(diacetylamino)-1-methyl-prop-1-enyl acetate 

Downstream Products

• 13623-11-5 2,4,5-trimethylthiazole 
• 21392-51-8 2-amino-4,5-dimethyl-1H-pyrrole-3-carbonitrile 
• 21419-24-9 3-Amino-2-butanone hydrochloride 
• 109435-59-8 2-(3-methoxy-4-hydroxy-styryl)-3,4,5-trimethyl-oxazolium; iodide 
• 110394-93-9 2-(4-dimethylamino-styryl)-3,4,5-trimethyl-oxazolium; iodide 
• 110180-08-0 2-[2-(4-diethylamino-anilino)-vinyl]-3,4,5-trimethyl-oxazolium; iodide 
• 109495-85-4 2-[2-(4-ethoxycarbonyl-anilino)-vinyl]-3,4,5-trimethyl-oxazolium; iodide 
• 108874-85-7 3,4,5-trimethyl-2-(4-nitro-styryl)-oxazolium; iodide 
• 110513-33-2 2-[2-(4-ethoxy-anilino)-vinyl]-3,4,5-trimethyl-oxazolium; iodide 
• 109474-86-4 2-[2-(4-methoxy-anilino)-vinyl]-3,4,5-trimethyl-oxazolium; iodide 
• 110937-57-0 2-(2-hydroxy-styryl)-3,4,5-trimethyl-oxazolium; iodide 
• 109474-85-3 3,4,5-trimethyl-2-[2-(4-methyl-anilino)-vinyl]-oxazolium; iodide 
• 109259-68-9 2-(2-anilino-vinyl)-3,4,5-trimethyl-oxazolium; iodide 
• 109670-14-6 3,4,5-trimethyl-2-(4-phenyl-buta-1,3-dienyl)-oxazolium; iodide 

Relevant academic research and scientific papers

Identification of new pyrrolo[2,3-d]pyrimidines as potent VEGFR-2 tyrosine kinase inhibitors: Design, synthesis, biological evaluation and molecular modeling

Vascular endothelial growth factor receptor-2 (VEGFR-2) plays a crucial role in cancer angiogenesis. In the current study, a series of novel pyrrolo[2,3-d]pyrimidine based-compounds was designed and synthesized as VEGFR-2 inhibitors, in accordance to the structure activity relationship (SAR) studies of known type II VEGFR-2 inhibitors. The newly synthesized compounds were evaluated for their ability to inhibit VEGFR-2 kinase enzyme in vitro. All the tested compounds demonstrated highly potent dose-related VEGFR-2 inhibition with IC50 values in nanomolar range. Among these compounds, pyrrolo[2,3-d]pyrimidine derivatives carrying biaryl urea moieties (12d and 15c) exhibited IC50 values of 11.9 and 13.6 nM respectively. Additionally, most of the newly synthesized final compounds were tested on 60 human cancer cell lines. Docking of these compounds into the inactive conformation of VEGFR-2 was performed which showed comparable binding modes to that of the FDA approved VEGFR-2 kinase inhibitors. These newly discovered potent kinase inhibitors could be considered as potential candidates for the development of new targeted anticancer agent.

The Enantioselective Dakin-West Reaction

Here we report the development of the first enantioselective Dakin-West reaction, yielding α-acetamido methylketones with up to 58 % ee with good yields. Two of the obtained products were recrystallized once to achieve up to 84 % ee. The employed methylimidazole-containing oligopeptides catalyze both the acetylation of the azlactone intermediate and the terminal enantioselective decarboxylative protonation. We propose a dispersion-controlled reaction path that determines the asymmetric reprotonation of the intermediate enolate after the decarboxylation.

Asymmetric transfer hydrogenation of α,β-unsaturated, α-tosyloxy and α-substituted ketones

Asymmetric transfer hydrogenation of cyclic and acyclic α,β-unsaturated ketones catalysed by η6-p-cymene/ ruthenium(II) and η5-pentamethylcyclopentadienyl/rhodium(III) complexes have been investigated. Cyclic α,β-unsaturated ketones appeared to be more suitable substrates for the synthesis of enantiomerically pure allylic alcohols than do acyclic α,β-unsaturated ketones. A proposed mechanism for the formation of 4-phenyl-[1,3]-dioxolan-2-one from α-tosyloxy- and halo-substituted acetophenones is discussed. The results of further investigations into the reduction of a range of α- tosyloxyacetophenones and the dynamic kinetic resolution of α-substituted ketones is presented.

Broad spectrum chemistry as practised by Novartis process research

Three actual examples from the current product palette within Novartis Process Research will demonstrate the some of the variety and challenges encountered in modern chemical development.

Asymmetric reduction of cyclic enones to allylic alcohols

Asymmetric transfer hydrogenation of cyclic enones results in highly enantioselective reduction to cyclic allylic alcohols.

Large-scale synthesis of a pyrrolo[2,3-d]pyrimidine via Dakin-West reaction and Dimroth rearrangement

Pyrrolo[2,3-d]pyrimidines have been widely investigated as pharmaceutically active compounds. In this article, we present a short and efficient synthesis of 4-(3-chlorophenylamino)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine starting from cheap alanine and malononitrile. To the best of our knowledge, the first application of a Dakin-West reaction on plant scale is demonstrated by elaboration of a modified procedure avoiding uncontrolled release of carbon dioxide. Pyrimidine ring formation is achieved in a simple one-pot reaction which is followed by an equally simple isomerization. The whole synthesis requires neither chromatographies nor extractions, no waste treatment and no special equipment, resulting in a remarkably ecological as well as economical process.

Reaction of 3-(Acetoxyamino)quinazolin-4(3H)-ones with Enolic β-Diketones: the N-N Bond as a Chiral Axis in N-(3,4-dihydro-4-oxoquinazolin-3-yl)-N-acyl-α-aminoketones; Reductive and Base-catalysed Cleavage of the N-N Bond in N-Acetyl-N-(3,4-dihydro-4-oxoquinazolin-3-yl)-α-amino Aci...

Following the method of Foucaud and coworkers, reaction of pentane-2,4-dione with 3-(acetoxyamino)quinazolin-4-one 8 gave the keto amide 9 (15percent). 3-Methylpentane-2,4-dione reacts with compound 8 to give a relatively stable enol 11 (66percent) which can be isolated in a crystalline form.Rotation around the N-N bonds in both compounds 9 and 11 is believed to be slow on the real time-scale and hence the N-N bonds can be considered as a chiral axes.As a result, protonation of the enol double bond in compound 11 and the creation of an additional chiral centre, gives rise to the separable keto amides 14 and 15; this protonation can be accomplished completely diastereoselectively.Lead tetraacetate acetoxylation of compound 11 to give compound 11 to give compound 19 is also completely diastereoselective.Brief heating of the enol effects the elimination of the quinazolinone and the formation of the N-acetylimine 16 via an 8-membered transition state.Base-catalysed elimination of the quinazolinone ring from compound 22 is surprisingly easy: reductive cleavage of this N-N bond in compound 22 is facile by comparison with the 3-(alkylamino)quinazolin-4-ones.

Studies on organophosphorus compounds 55. A new and facile synthetic route to 1-alkyl(aryl)-2-amino-1-hydroxyalkylphosphonic acids

Nucleophilic addition of dimethyl phosphite to acylamino ketones prepared conveniently by the Dakin-West reaction involving reaction of the corresponding α-amino acids and acid anhydrides, followed by subsequent hydrolysis affords 1-alkyl(aryl)-2-amino-1-hydroxyalkylphosphonic acids in satisfactory yield.

Synthesis of 4-oxopyrrolopyrimidine-3-carboxylic acid derivatives as potential antimicrobial agents

A route for the synthesis of various derivatives of 4-oxopyrrolopyrimidine-3-carboxylic acid from 2-amino-3-cyano-4,5-dimethylpyrrole and 2-amino-3-cyano-4-arylpyrroles is described.

Specific Inhibitors in Vitamin Biosynthesis. Part 8. Syntheses of some Functionalised 7,7-Dialkyl-7,8-dihydropterins

The synthesis of variety of functionalised blocked 7,8-dihydropteridines is described.The functional groups were chosen to provide compounds with potential for investigating the protein chemistry of enzymes in the pathway leading to dihydrofolate and, in particular, of 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase.The potential of 7-substituents to provide sites of attachment of inhibitors to columns for affinity chromatography was explored but the extent of the study was curtailed by the restricted applicability of nitrosyl chloride addition to alkenes, a reaction used in the synthesis of pteridine precursors.The syntheses of two compounds, a 6-trichlorophenoxymethyldihydropteridine and of a thiadiazolopteridine, designed to have enchanced transport properties, are also described.