634602-84-9

Basic information

• Product Name: ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate
• Synonyms: ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate;Ethyl 2-hydroxy-1H-1,3-benzodiazole-6-carboxylate;ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate-3
• CAS NO: 634602-84-9
• Molecular Formula: C10H10N2O3
• Molecular Weight: 206.198
• Mol File: 634602-84-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate(634602-84-9)
• EPA Substance Registry System: ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate(634602-84-9)

Safety Data

• Hazardous Substances Data: 634602-84-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate is used as a synthetic intermediate for the development of benzimidazole-based pharmaceuticals. Its role in the synthesis of these compounds is crucial due to their diverse biological activities, such as anticancer, antimicrobial, antiviral, and antihelminthic properties. This makes it a promising candidate for the creation of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate is utilized as a precursor in the synthesis of benzimidazole-based pesticides. Its involvement in the production of these agrochemicals is significant due to the broad-spectrum activity of benzimidazoles against various pests and diseases, contributing to enhanced crop protection and yield.
The synthesis and properties of ethyl 2-oxo-2,3-dihydro-1H-benzo[d]iMidazole-5-carboxylate are of keen interest to the scientific and pharmaceutical communities, as they seek to explore and expand its potential applications in both the medical and agricultural fields.

Upstream product

• 37466-90-3 ethyl 3,4-diaminobenzoate 
• 57-13-6 urea 

Downstream Products

• 857035-29-1 2-chloro-3H-benzoimidazole-5-carboxylic acid ethyl ester 
• 857070-67-8 [2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazol-5-yl]methanol 
• 857070-65-6 3-(3-hydroxy-6-methylpyridin-2-ylmethyl)-2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazole-5-carbaldehyde 
• 857067-39-1 2-[5-hydroxymethyl-2-(3-morpholin-4-ylpropylamino)benzoimidazol-1-ylmethyl]-6-methylpyridin-3-ol 
• 857067-38-0 2-[6-hydroxymethyl-2-(3-morpholin-4-ylpropylamino)benzoimidazol-1-ylmethyl]-6-methylpyridin-3-ol 
• 857070-66-7 (2-chloro-3H-benzoimidazol-5-yl)methanol 

Relevant articles and documents

Selection of a respiratory syncytial virus fusion inhibitor clinical candidate. 2. Discovery of a morpholinopropylaminobenzimidazole derivative (TMC353121)

A preceding paper (Bonfanti et al. J. Med Chem. 2007, 50, 4572-4584) reported the optimization of the pharmacokinetic profile of substituted benzimidazoles by reducing their tissue retention. However, the modifications that were necessary to achieve this goal also led to a significant drop in anti-RSV activity. This paper describes a molecular modeling study followed by a lead optimization program that led to the recovery of the initial potent antiviral activity and the selection of TMC353121 as a clinical candidate.

HETEROCYCLYLAMINOALKYL SUBSTITUTED BENZIMIDAZOLES

Heterocyclylaminoalkyl Substituted Benzimidazoles Inhibitors of RSV replication of formula (I): The salts and stereochemically isomeric forms thereof, wherein Q is hydrogen, C1-6alkyl optionally substituted with a heterocycle or Q is C1 -6alkyl substituted with both -OR4 and a heterocycle; wherein said heterocycle is oxazolidine, thiazolidine, 1-oxo-thiazolidine, 1,1-dioxothiazolidine, morpholinyl, thiomorpholinyl, 1-oxo-thiomorpholinyl, 1,1-dioxothiomorpholinyl, hexahydrooxazepine, hexahydrothiazepine, 1-oxo-hexahydrothiazepine, 1,1-dioxo-hexahydrothiazepine, pyrrolidine, piperidine, homopiperidine, piperazine; which heterocyle may be substituted with 1-2 substituents; each Alk is C1 -6alkanediyl; R1 is Ar or optionally substituted piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydrofuranyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazo lyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazolyl, benzthiazolyl, pyridopyridyl, naphthiridinyl, 1H-imidazo[4,5-b]pyridinyl, 3H-imidazo[4,5-b]pyridinyl, imidazo[1,2-a]pyridinyl or 2,3-dihydro-1,4-dioxino[2,3-b]pyridyl; R3 is hydroxyC1 -6alkyl, C1 -6alkoxyC1-6alkyl, cyanoC1-6alkyl, aminocarbonyl-C1 -6-alkyl, mono-or di(C1 -6alkyl)aminocarbonyl-C1 -6- alkyl, carboxyl-C1 -6-alkyl, C1-6alkoxycarbonyl-C1-6 alkyl; R2, R4 and R5 are hydrogen or C1-6alkyl; Het is pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, furanyl, tetrahydrofuranyl, thienyl, pyrrolyl, thiazolyl, oxazolyl, imidazolyl, isothiazolyl, pyrazolyl, isoxazolyl, oxadiazolyl, quinolinyl, quinoxalinyl, benzofuranyl, benzothienyl, benzimidazolyl, benzoxazo lyl, benzthiazolyl, pyridopyridyl, naphthiridinyl, 1H-imidazo[4,5-b]- pyridinyl, 3H-imidazo[4,5-b]pyridinyl, imidazo[1,2-a]pyridinyl and 2,3-dihydro-1,4- dioxino[2,3-b]pyridyl; Ar is optionally substituted phenyl; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I).

5- OR 6-SUBSTITUTED BENZIMIDAZOLE DERIVATIVES AS INHIBITORS OF RESPIRATORY SYNCYTIAL VIRUS REPLICATION

The present invention concerns 5- or 6-substituted-benzimidazole derivatives having inhibitory activity on the replication of the respiratory syncytial virus and having the formula (I) a prodrug, N-oxide, addition salt, quaternary amine, metal complex or

MORPHOLINYL CONTAINING BENZIMIDAZOLES AS INHIBITORS OF RESPIRATORY SYNCYTIAL VIRUS REPLICATION

The present invention concerns morpholinyl containing benzimidazoles having inhibitory activity on the replication of the respiratory syncytial virus and having the formula (I), a prodrug, N-oxide, addition salt, quaternary amine, metal complex or stereoc