101385-69-7

Usage

Chemical Properties

White crystalline powder

Uses

Reactant for synthesis of: Diazo-transfer reagents Reagent for synthesis of: Cannabinoid CB1 receptor agonists Selective small-molecule melanocortin-4 receptor agonists Imidazoles as selective cannabinoid CB2 receptor antagonists Cyclic alpha-peptoids Cyclic melanotropin peptide analogues selective for the human melanocortin-4 receptor

InChI:InChI=1/C5H11ClN2.F6P/c1-7-3-4-8(2)5(7)6;1-7(2,3,4,5)6/h5H,3-4H2,1-2H3;/q;-1/p+1

Upstream product

• 81759-25-3 1,1'-carbonyldipyrrolidine 
• 80-73-9 1,3-dimethyl-2-imidazolidinone 
• 37091-73-9 2-chloro-1,3-dimethylimidazolinium chloride 

Downstream Products

• 1266134-54-6 2-azido-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate (V) 
• 123377-20-8 2-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-1,3-dimethyl-4,5-dihydro-1H-imidazol-3-ium hexafluorophosphate 

Relevant academic research and scientific papers

2-Azido-1,3-dimethylimidazolinium salts: Efficient diazo-transfer reagents for 1,3-dicarbonyl compounds

We have developed the diazo-transfer of 2-azido-1,3-dimethylimidazolinium salts to 1,3-dicarbonyl compounds. 2-Azido-1,3-dimethylimidazolinium chloride (ADMC) was prepared by N-nitrosation of N-aminoguanidine or by the reaction of 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and sodium azide. The corresponding phosphate, ADMP, was isolated as a crystal, and was found to be a stable and safe reagent. Both ADMC and ADMP reacted with 1,3-dicarbonyl compounds under mild conditions to give 2-diazo-1,3-dicarbonyl compounds in high yields, which are easily isolated because the by-products are highly soluble in water. Georg Thieme Verlag Stuttgart.

One-Pot Synthesis of Nucleotides and Conjugates in Aqueous Medium

Herein, we describe a one-pot synthesis, in a mixture of water/acetonitrile, of nucleoside 5′-polyphosphates and some derivatives starting from their corresponding nucleoside 5′-monophosphates. Phosphorimidazolide intermediates are formed in the presence of imidazole and 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate. Under these mild conditions, nucleoside 5′-di- and 5′-triphosphates, dinucleoside 5′,5′-polyphosphates, as well as some nucleotide analogues modified either on the nucleoside or on the phosphate moieties are obtained in moderate to high yields.

Applications of Shoda's reagent (DMC) and analogues for activation of the anomeric centre of unprotected carbohydrates

2-Chloro-1,3-dimethylimidazolinium chloride (DMC, herein also referred to as Shoda's reagent) and its derivatives are useful for numerous synthetic transformations in which the anomeric centre of unprotected reducing sugars is selectively activated in aqueous solution. As such unprotected sugars can undergo anomeric substitution with a range of added nucleophiles, providing highly efficient routes to a range of glycosides and glycoconjugates without the need for traditional protecting group manipulations. This mini-review summarizes the development of DMC and some of its derivatives/analogues, and highlights recent applications for protecting group-free synthesis.

Protecting-group-free one-pot synthesis of glycoconjugates directly from reducing sugars

The conversion of sugars into glycomimetics typically involves multiple protecting-group manipulations. The development of methodology allowing the direct aqueous conversion of free sugars into glycosides, and mimics of oligosaccharides and glycoconjugates in a high-yielding and stereoselective process is highly desirable. The combined use of 2-azido-1,3-dimethylimidazolinium hexafluorophosphate and the Cu-catalyzed Huisgen cycloaddition allowed the synthesis of a range of glycoconjugates in a one-step reaction directly from reducing sugars under aqueous conditions. The reaction, which is completely stereoselective, may be applied to the convergent synthesis of triazole-linked glycosides, oligosaccharides, and glycopeptides. The procedure provides a method for the one-pot aqueous ligation of oligosaccharides and peptides bearing alkyne side chains.

A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.

Substituted guanidines: Introducing diversity in combinatorial chemistry

(matrix presented) The guanidine moiety is an important motif present in many biologically active compounds. Fully substituted guanidines are of key importance for the development of bioactive molecules. The present paper reports on an efficient procedure for the direct solid-phase conversion of amines to fully substituted guanidines under very mild conditions.