53786-47-3

Basic information

• Product Name: ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate
• Synonyms: ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate;4-(2-Oxo-2,3-dihydro-1H-benzoimidazole-1-yl)piperidine-1-carboxylic acid ethyl ester;4-[(2,3-Dihydro-2-oxo-1H-benzimidazol)-1-yl]-1-piperidinecarboxylic acid ethyl ester;Einecs 258-777-9
• CAS NO: 53786-47-3
• Molecular Formula: C₁₅H₁₉N₃O₃
• Molecular Weight: 289.32966
• EINECS: 258-777-9
• Mol File: 53786-47-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.272g/cm³
• Refractive Index: 1.587
• CAS DataBase Reference: ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate(53786-47-3)
• EPA Substance Registry System: ethyl 4-(2,3-dihydro-2-oxo-1H-benzimidazol-1-yl)piperidine-1-carboxylate(53786-47-3)

Safety Data

• Hazardous Substances Data: 53786-47-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H19N3O3/c1-2-21-15(20)17-9-7-11(8-10-17)18-13-6-4-3-5-12(13)16-14(18)19/h3-6,11H,2,7-10H2,1H3,(H,16,19)

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 87120-77-2 ethyl 4-((2-aminophenyl)amino)piperidine-1-carboxylate 
• 906532-70-5 4-[1-(2-bromo-phenyl)ureido]piperidine-1-carboxylic acid ethyl ester 
• 906532-69-2 4-[1-(2-chloro-phenyl)ureido]piperidine-1-carboxylic acid ethyl ester 
• 906532-71-6 4-[1-(2-iodo-phenyl)ureido]piperidine-1-carboxylic acid ethyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 959700-75-5 1,3-dihydrospiro[2H-benzimidazole-2,4'-piperidine]-1'-carboxylic acid ethyl ester 
• 85443-52-3 ethyl 4-((2-nitrophenyl)amino)piperidine-1-carboxylate 
• 58859-46-4 ethyl 4-aminopiperidine-1-carboxylate 
• 615-43-0 2-iodophenylamine 
• 63260-44-6 4-(2-chloro-anilino)-piperidine-1-carboxylic acid ethyl ester 
• 95-51-2 o-chloroaniline 
• 29976-53-2 N-ethoxycarbonyl-4-piperidone 
• 615-36-1 2-bromoaniline 

Downstream Products

• 20662-53-7 4-(2-keto-1-benzimidazolinyl)piperidine 
• 400797-16-2 1-(1-{3-[5-acetyl-3-(4-trifluoromethyl-phenyl)-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-1-yl]-2-hydroxy-propyl}-piperidin-4-yl)-1,3-dihydro-benzoimidazol-2-one 
• 53786-10-0 1,3-dihydro-1-methyl-3-(4-piperidinyl)-2H-benzimidazol-2-one 
• 1469924-36-4 C₂₃H₂₅Cl₂N₃O₃ 
• 1469924-66-0 C₄₂H₅₂Cl₂N₆O₆ 
• 1469924-67-1 C₄₈H₅₇FN₆O₆ 

Relevant articles and documents

Novel BQCA- and TBPB-Derived M1 Receptor Hybrid Ligands: Orthosteric Carbachol Differentially Regulates Partial Agonism

Recently, investigations of the complex mechanisms of allostery have led to a deeper understanding of G protein-coupled receptor (GPCR) activation and signaling processes. In this context, muscarinic acetylcholine receptors (mAChRs) are highly relevant due to their exemplary role in the study of allosteric modulation. In this work, we compare and discuss two sets of putatively dualsteric ligands, which were designed to connect carbachol to different types of allosteric ligands. We chose derivatives of TBPB [1-(1′-(2-tolyl)-1,4′-bipiperidin-4-yl)-1H-benzo[d]imidazol-2(3H)-one] as M1-selective putative bitopic ligands, and derivatives of benzyl quinolone carboxylic acid (BQCA) as an M1 positive allosteric modulator, varying the distance between the allosteric and orthosteric building blocks. Luciferase protein complementation assays demonstrated that linker length must be carefully chosen to yield either agonist or antagonist behavior. These findings may help to design biased signaling and/or different extents of efficacy.

Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

A synthetically useful protocol has been developed for the preparation of highly functionalized N-alkenyl-benzimidazol-2-ones. Reaction of commercially available o-phenylenediamines with variously substituted cyclic ketones provides spiro-benzimidazolines. Treatment of these spiro-benzimidazolines with triphosgene in the presence of potassium carbonate results in rapid rearrangement and formation of N-alkenyl-benzimidazol-2-ones in modest to excellent yield for the two-step sequence. Extension of this methodology toward the preparation of a μ opiate receptor antagonist and droperidol, a potent antiemetic and antipsychotic agent, currently a marketed pharmaceutical is also described. Upon treatment of spiro-benzimidazolines with triphosgene in the presence of sodium triacetoxyborohydride, N-alkyl-benzimidazol-2-ones were formed.

Benzodiazepine calcitonin gene-related peptide (CGRP) receptor antagonists: Optimization of the 4-substituted piperidine

In our continuing effort to identify CGRP receptor antagonists for the acute treatment of migraine, we have undertaken a study to evaluate alternative 4-substituted piperidines to the lead dihydroquinazolinone 1. In this regard, we have identified the piperidinyl-azabenzimidazolone and phenylimidazolinone structures which, when incorporated into the benzodiazepine core, afford potent CGRP receptor antagonists (e.g., 18 and 29). These studies produced a potent analog (18) which overcomes the instability issues associated with the lead structure 1. A general pharmacophore for the 4-substituted piperidine component of these CGRP receptor antagonists is also presented.