92289-43-5

Upstream product

• 530-62-1 1,1'-carbonyldiimidazole 
• 100-61-8 N-methylaniline 
• 288-32-4 1H-imidazole 
• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 

Downstream Products

• 99839-93-7 N-methyl-N-phenyl-carbamoyl cyanide 
• 82504-15-2 1,1-diisopropyl-3-methyl-3-phenylurea 
• 701919-20-2 N'-cyclohexyl-N-methyl-N-phenylurea 
• 85149-52-6 N-methyl-N-phenyl-1H-indole-3-carboxamide 
• 1392831-43-4 1-(4-cyanophenyl)-3-methyl-1,3-diphenylurea 
• 1392831-42-3 1-(4-cyanophenyl)-1,3-dimethyl-3-phenylurea 
• 1392831-41-2 1-(4-chlorophenyl)-1,3-dimethyl-3-phenylurea 
• 1392831-45-6 N-methyl-N-phenyl-3,4-dihydroquinoline-1(2H)-carboxamide 
• 1392831-36-5 N-methyl-N-phenylindoline-1-carboxamide 
• 1392831-44-5 N-methyl-N-phenyl-3,5-dimethylpyrazole-1-carboxamide 
• 897839-65-5 1-methyl-1-phenyl-3-(thiazol-2-yl)urea 
• 112449-25-9 3-(4-fluorophenyl)-1-methyl-1-phenylurea 
• 101112-21-4 N-methyl-N-phenyl-N’-phenylurea 
• 1216909-88-4 C₁₁H₁₆N₂O₂ 

Relevant academic research and scientific papers

Discovery of a Potent, Long-Acting, and CNS-Active Inhibitor (BIA 10-2474) of Fatty Acid Amide Hydrolase

Fatty acid amide hydrolase (FAAH) can be targeted for the treatment of pain associated with various medical conditions. Herein we report the design and synthesis of a novel series of heterocyclic-N-carboxamide FAAH inhibitors that have a good alignment of potency, metabolic stability and selectivity for FAAH over monoacylglycerol lipase (MAGL) and carboxylesterases (CEs). Lead optimization efforts carried out with benzotriazolyl- and imidazolyl-N-carboxamide series led to the discovery of clinical candidate 8 l (3-(1-(cyclohexyl(methyl)carbamoyl)-1H-imidazol-4-yl)pyridine 1-oxide; BIA 10-2474) as a potent and long-acting inhibitor of FAAH. However, during a Phase I clinical trial with compound 8 l, unexpected and unpredictable serious neurological adverse events occurred, affecting five healthy volunteers, including the death of one subject.

Solvent-Free Synthesis of Cyanoformamides from Carbamoyl Imidazoles

A straightforward and solvent-free synthesis of various secondary and tertiary cyanoformamides from carbamoyl imidazoles and TMSCN has been developed. Both cyclic and acyclic carbamoyl imidazoles react smoothly to form the relevant cyanoformamides in excellent yields, often within minutes.

A facile method for the preparation of unsymmetrical ureas utilizing zirconium (IV) chloride

A facile synthetic method for the preparation of unsymmetrical ureas from amines is described. Carbamoyl imidazole compounds were prepared by the reaction of 1, 1-carbonyldiimidazole with primary or secondary amines, and further activation by treatment with zirconium(IV) chloride to generate the desired urea. This reaction protocol was applied to the synthesis of tri and tetrasubstituted ureas with high yields. This study provides an alternative guideline for the practical preparation of various unsymmetrical ureas.

PHARMACEUTICAL COMPOUNDS

The invention relates to compounds and compositions for inhibiting the enzyme fatty acid amide hydrolase (FAAH), the use of the compounds in therapy and, in particular, for treating or preventing conditions whose development or symptoms are linked to subs

Unprecedented "in water" imidazole carbonylation: Paradigm shift for preparation of urea and carbamate

The first "In Water" imidazolecarbonylation of amine is described. A one pot reaction of carbonylimidazolide in water with a nucleophile provides an efficient and general method for the preparation of urea, carbamates and thiocarbamates. Use of an anhydrous solvent and an inert atmosphere could be avoided. Product precipitate out from the reaction mixture and can be obtained in high purity by filtration, resulting in a simple and scalable method.

Unsymmetrical tetrasubstituted ureas from tertiary carbamoylimidazole: Activation by AlMe3

An efficient and general method for the synthesis of unsymmetrical tetrasubstituted ureas from carbamoylimidazole is described. The conversion is achieved by the concurrent quarternization of the imidazole nitrogen and activation of amines with AlMe3. The Royal Society of Chemistry 2012.

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Lithiation of N-aryl S-α-alkylbenzyl thiocarbamates leads to rearrangement with migration of the N-aryl ring to the anionic centre α to S, a process which generally proceeds with ca. 98% retention of stereochemistry and returns chiral benzylic tertiary thiols in high enantiomeric ratios.

Carbamoylimidazolium and thiocarbamoylimidazolium salts: Novel reagents for the synthesis of ureas, thioureas, carbamates, thiocarbamates and amides

Carbamoylimidazolium salts act as efficient N,N-disubstituted carbamoylating reagents. These salts are readily prepared by the sequential treatment of secondary amines with N,N′-carbonyldiimidazole (CDI) and iodomethane. The carbamoylimidazolium salts are more efficient carbamoyl transfer reagents than the intermediate carbamoylimidazoles, as a result of the 'imidazolium' effect. Kinetic studies on the base promoted hydrolysis of both carbamoylimidazoles and carbamoylimidazolium salts reveal over a hundred-fold rate acceleration. The salts react with amines, thiols, phenols/alcohols, and carboxylic acids in high yields, without the need for subsequent chromatographic purification of the products, producing ureas, thiocarbamates, carbamates, and amides, respectively. Analogous thiocarbamoylimidazolium salts were also synthesized from secondary amines and N,N′-thiocarbonyldiimidazole (TCDI), followed by methylation with iodomethane.

A new protocol for the formation of carbamates and thiocarbamates using carbamoyl imidazolium salts

Carbamoyl imidazolium salts are demonstrated to act as useful carbamoylation reagents, in reactions with alcohols, phenols, thiols and thiophenols to form carbamates and thiocarbamates under relatively mild conditions. The salts are stable and easily prepared from the corresponding amines using CDI.

An efficient new protocol for the formation of unsymmetrical Tri-and tetrasubstituted ureas

A new method for producing unsymmetrical, tetrasubstituted ureas from N, N'carbonyldiimidazole (CDI) is presented. Carbamoyl imidazolium salts are prepared from the reaction of CDI with a secondary amine, followed by alkylation with MeI. Secondary amines add with ease to imidazolium salts at room temperature to give unsymmetrical, tetrasubstituted ureas in excellent yields.