530084-74-3

Basic information

• Product Name: (8-(benzyloxy)-5-[(1R)-2-broMo-1-{[tert-butyl(diMethyl)silyl]oxy}ethyl]quinolin-2(1H)-one )
• Synonyms: (8-(benzyloxy)-5-[(1R)-2-broMo-1-{[tert-butyl(diMethyl)silyl]oxy}ethyl]quinolin-2(1H)-one );(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-one;8-Benzyloxy-5-[(R)-2-bromo-1-[(tert-butyldimethylsilyl)oxy]ethyl]-1H-quinolin-2-one
• CAS NO: 530084-74-3
• Molecular Formula: C₂₄H₃₀BrNO₃Si
• Molecular Weight: 488.4894
• Mol File: 530084-74-3.mol
• Article Data: 27

Chemical Properties

• Boiling Point: 571.4°C at 760 mmHg
• Flash Point: 299.4°C
• Appearance: /
• Density: 1.237g/cm³
• Vapor Pressure: 4.57E-13mmHg at 25°C
• Refractive Index: 1.562
• PKA: 10.75±0.70(Predicted)
• CAS DataBase Reference: (8-(benzyloxy)-5-[(1R)-2-broMo-1-{[tert-butyl(diMethyl)silyl]oxy}ethyl]quinolin-2(1H)-one )(CAS DataBase Reference)
• NIST Chemistry Reference: (8-(benzyloxy)-5-[(1R)-2-broMo-1-{[tert-butyl(diMethyl)silyl]oxy}ethyl]quinolin-2(1H)-one )(530084-74-3)
• EPA Substance Registry System: (8-(benzyloxy)-5-[(1R)-2-broMo-1-{[tert-butyl(diMethyl)silyl]oxy}ethyl]quinolin-2(1H)-one )(530084-74-3)

Safety Data

• Hazardous Substances Data: 530084-74-3(Hazardous Substances Data)

Usage

Description

(8-(benzyloxy)-5-[(1R)-2-brom0-1-[tert-butyl(dimethyl)silyl]oxyethyl]quinolin-2(1H)-one) is a complex organic molecule characterized by a quinoline ring system with a benzyloxy group at the 8-position and a bromo and a silyl group at the 5-position. The presence of a quinoline moiety, a common structural motif in pharmaceuticals and bioactive compounds, suggests that this chemical may possess significant biological activity. The inclusion of a bromo and silyl group indicates potential applications in organic synthesis as a versatile building block for constructing more complex molecules. The tert-butyl group in the silyl moiety provides steric protection, enhancing the compound's stability and utility in chemical reactions.

Uses

Used in Pharmaceutical Industry:
(8-(benzyloxy)-5-[(1R)-2-brom0-1-[tert-butyl(dimethyl)silyl]oxyethyl]quinolin-2(1H)-one) is used as a potential bioactive compound for its quinoline moiety, which is commonly found in many pharmaceuticals. Its unique structure may contribute to the development of new drugs with specific therapeutic effects.
Used in Organic Synthesis:
In the field of organic synthesis, (8-(benzyloxy)-5-[(1R)-2-brom0-1-[tert-butyl(dimethyl)silyl]oxyethyl]quinolin-2(1H)-one) serves as a versatile building block for creating more complex molecules. The presence of a bromo and silyl group allows for further chemical modifications and functionalization, expanding its utility in the synthesis of novel organic compounds.
Used in Chemical Reactions:
(8-(benzyloxy)-5-[(1R)-2-brom0-1-[tert-butyl(dimethyl)silyl]oxyethyl]quinolin-2(1H)-one) is utilized in chemical reactions due to its stability, conferred by the steric protection of the tert-butyl group in the silyl moiety. This stability makes it a valuable intermediate in various chemical processes, potentially leading to the production of new and useful compounds.

InChI:InChI=1/C24H30BrNO3Si/c1-24(2,3)30(4,5)29-21(15-25)18-11-13-20(23-19(18)12-14-22(27)26-23)28-16-17-9-7-6-8-10-17/h6-14,21H,15-16H2,1-5H3,(H,26,27)/t21-/m0/s1

Upstream product

• 69739-34-0 t-butyldimethylsiyl triflate 
• 108-48-5 2,6-dimethylpyridine 
• 530084-79-8 8-(benzyloxy)-5-[(1R)-2-bromo-1-hydroxyethyl]quinolin-2(1H)-one 
• 107-83-5 2-Methylpentane 
• 144-55-8 sodium hydrogencarbonate 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 100331-89-3 8-benzyloxy-5-(2-bromoacetyl)-1H-quinolin-2-one 
• 93609-84-8 5-acetyl-8-benzyloxy-1H-quinolin-2-one 

Downstream Products

• 530084-80-1 8-benzyloxy-5-[(R)-2-[2-(4-bromo-phenyl)-ethylamino]-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-quinolin-2-one hydrochloride 
• 743460-26-6 (R)-5-(2-(benzylamino)-1-((tert-butyldimethylsilyl)oxy)ethyl)-8-(benzyloxy)quinolin-2(1H) one 
• 1415970-74-9 (1-(9-((2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)nonyl)piperidin-4-yl)methyl 2-cyclohexyl-2-hydroxy-2-phenylacetate 
• 1416065-91-2 (R)-quinuclidin-3-yl (3-(9-((R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)nonyloxy)phenyl)-(phenyl)methylcarbamate 
• 1346655-28-4 (R)-N-(4-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)(methyl)amino)pent-1-yn-1-yl)phenyl)-2,2,2-trifluoroacetamide 
• 1346655-75-1 (R)-6-[[3-[[8-[[2-[(tert-butyldimethylsilyl)oxy]-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide 
• 1346655-85-3 (R)-6-((3-((3-(5-((2-((tert-butyldimethylsilyl)oxy)-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl)amino)pent-1-yn-1-yl)phenyl)carbamoyl)phenyl)sulfonyl)-4-((3-methoxyphenyl)amino)-8-methylquinoline-3-carboxamide 
• 1346653-88-0 (R)-6-[[3-[[8-[[2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino]octyl]carbamoyl]phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide 
• 1346654-58-7 (R)-8-(benzyloxy)-5-(1-((tert-butyldimethylsilyl)oxy)-2-(methylamino)ethyl)quinolin-2(1H)-one 
• 865874-73-3 (R)-methyl 3-(2-((2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-2-methylpropyl)benzoate 
• 1346424-77-8 (R)-3-(2-((2-(8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl)-2-((tert-butyldimethylsilyl)oxy)ethyl)amino)-2-methylpropyl)benzoic acid 
• 1346655-67-1 (R)-6-[[3-[[4-[2-[[2-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-[(tert-butyldimethylsilyl)oxy]ethyl]amino]ethyl]phenyl]carbamoyl]-phenyl]sulfonyl]-4-[(3-methoxyphenyl)amino]-8-methylquinoline-3-carboxamide 
• 312753-06-3 indacaterol 
• 753498-25-8 indacaterol maleate 

Relevant articles and documents

Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.

Carbamide derivative and preparation method thereof

The invention discloses a carbamide derivative and a preparation method thereof. The present invention relates to a compound represented by a general formula (I) or a stereoisomer, a hydrate, a metabolite, a solvate, a pharmaceutically acceptable salt, a co-crystal or a prodrug thereof, a preparation method and applications of the derivative in preparation of drugs for treatment of airway obstructive diseases; the compound represented by the general formula (I) is shown in the specification, and wherein definitions of substituents are consistent with those in the specification.

Synthesis method of indacaterol and salt derivatives thereof and intermediate for the synthesis

The invention belongs to the technical field of drug synthesis, and particularly relates to a synthesis method of indacaterol and salt derivatives thereof and intermediate for the synthesis. The synthesis method of indacaterol comprises the following steps: carrying out amine alkylation and deprotection reaction, in a one-pot manner, on a compound shown as a general formula IV and a compound shownas a formula V serving as raw materials to obtain a compound shown as a formula I, wherein the reaction equation is shown as the specification; wherein R is a silane protecting group. According to the technical scheme provided by the invention, by carrying out Boc protection on the amino group, polyalkylation on the amino group is ingeniously avoided, so that under the condition that both the hydroxyl group and the amino group have proper protection, the alkylation reaction effectively avoids the generation of by-products; after the alkylation reaction, hydroxyl and amino deprotection can bedirectly carried out, so that the multi-step reaction is completed in one reactor; according to the method, the intermediate purification and separation process is omitted, the reaction yield is increased to the maximum extent, and the production cost is reduced.