503859-27-6

Basic information

• Product Name: 3-AMINO-4-(CYCLOHEXYLAMINO) BENZOIC ACID METHYL ESTER
• Synonyms: 3-AMINO-4-(CYCLOHEXYLAMINO) BENZOIC ACID METHYL ESTER;Benzoic acid, 3-amino-4-(cyclohexylamino)-,methyl ester;Methyl 3-aMino-4-(cyclohexylaMino)benzoate
• CAS NO: 503859-27-6
• Molecular Formula: C₁₄H₂₀N₂O₂
• Molecular Weight: 248.3208
• Mol File: 503859-27-6.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-AMINO-4-(CYCLOHEXYLAMINO) BENZOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-4-(CYCLOHEXYLAMINO) BENZOIC ACID METHYL ESTER(503859-27-6)
• EPA Substance Registry System: 3-AMINO-4-(CYCLOHEXYLAMINO) BENZOIC ACID METHYL ESTER(503859-27-6)

Safety Data

• Hazardous Substances Data: 503859-27-6(Hazardous Substances Data)

Upstream product

• 108-91-8 cyclohexylamine 
• 2365-85-7 3-amino-4-fluorobenzoic acid 
• 329020-79-3 3-amino-4-(cyclohexylamino)benzoic acid 
• 67-56-1 methanol 
• 96-99-1 4-chloro-3-nitrobenzoate 
• 14719-83-6 methyl 3-nitro-4-chlorobenzoate 
• 453-71-4 3-nitro-4-fluorobenzoic acid 
• 329-59-9 4-fluoro-3-nitro-benzoic acid methyl ester 
• 503859-26-5 N-cyclohexyl-4-methoxycarbonyl-2-nitroaniline 

Downstream Products

• 501371-91-1 1-cyclohexyl-2-(2-fluoro-4-hydroxyphenyl)-1H-benzimidazole-5-carboxylic acid methyl ester 
• 1430101-72-6 methyl 2-(3-(benzylamino)-2-phenylimidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-73-7 methyl 2-(3-(benzylamino)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-74-8 methyl 2-(3-(benzylamino)-2-(furan-2-yl)imidazo[1,2-a]pyridin-7-yl)-1-cyclohexyl-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-75-9 methyl 1-cyclohexyl-2-(3-(cyclohexylamino)-2-p-tolylimidazo[1,2-a]pyridin-7-yl)-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-76-0 methyl 1-cyclohexyl-2-(3-(cyclohexylamino)-2-(4-hydroxyphenyl)imidazo[1,2-a]pyridin-7-yl)-1H-benzo[d]imidazole-5-carboxylate 
• 1430101-87-3 C₂₀H₂₂N₄O₂ 
• 1519358-44-1 C₁₅H₂₂N₂O₂ 
• 1239608-90-2 methyl 6-oxo-8,8-dimethyl-11-cyclohexyl-5-(4-methoxyphenyl)-5,6,7,8,9,11-hexahydro-7H-4b,10,11-triazabenzo[b]fluorene-3-carboxylate 
• 503859-28-7 methyl 3-{[4-(benzyloxy)benzoyl]amino}-4-(cyclohexylamino)benzoate 
• 347173-48-2 1-cyclohexyl-2-(4-hydroxyphenyl)-1H-benzimidazole-5-carboxylic acid methyl ester 

Relevant articles and documents

Diversity-Oriented Synthesis of Coumarin-Linked Benzimidazoles via a One-Pot, Three-Step, Intramolecular Knoevenagel Cyclization

Diversity-oriented synthesis of coumarin-linked benzimidazoles from N-(2-aminophenyl)-2-cyanoacetamide was achieved via a one-pot, three-step sequential reaction in excellent yields. In situ intramolecular cyclization of the cyanoacetamide afforded benzimidazoles which subsequently underwent a Knoevenagel condensation of the 2-cyanomethylbenzimidazoles with salicylaldehydes promoted by triethylamine to reach the target compounds. An important intermediate, 2-(2-imino-2H-chromen-3-yl)-1H-benzimidazole was characterized by X-ray analysis and further hydrolyzed to 2-(coumarin-3-yl)benzimidazole in acidic condition. Among the synthesized compounds, some were found to be promising inhibitors of porcine kidney d-amino acid oxidase (pkDAO).

A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-b]quinazolin-1(1H)-ones

Ultrasound-assisted synthesis of benzimidazo[2,1-b]quinazolin-1(1H)-ones was achieved via piperidine-catalyzed three-component reaction of 2-aminobenzimidazoles, an aromatic aldehyde, and 1,3-dione in aqueous isopropanol. This mechanism was first suspected following our identification of unusual reaction intermediates in a one-pot reaction. An unprecedented coupling reaction, it involved a nucleophilic attack by 2-aminobenzimidazole on in situ generated Michael adduct, followed by electrocyclic ring formation reaction. In contrast to the commonly accepted mechanism, that the direct reaction of 2-amino benzimidazole with a Knoevenagel adduct cannot deliver target compounds.

Design and synthesis of conformationally restricted inhibitors of active thrombin activatable fibrinolysis inhibitor (TAFIa)

A series of 4,5,6,7-tetrahydro-1H-benzimidazole-5-carboxylic acid and 5,6,7,8-tetrahydroimidazo[1,2-a]pyridine-7-carboxylic acid derivatives designed as inhibitors of TAFIa has been prepared via a common hydrogenation-alkylation sequence starting from the appropriate benzimidazole and imidazopyridine system. We present a successful design strategy using a conformational restriction approach resulting in potent and selective inhibitors of TAFIa. The X-ray structure of compound 5 in complex with a H333Y/H335Q double mutant TAFI indicate that the conformational restriction is responsible for the observed potency increase.