139122-20-6

Basic information

• Product Name: 4-[2'-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-1,3-DIHYDRO-2H-INDOLE-2-ONE
• Synonyms: 4-[2'-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-1,3-DIHYDRO-2H-INDOLE-2-ONE;4-[2-[[(4-methylphenyl)sulfonyl]oxy]ethyl]-2-oxoindole;Ropinirole Intermediate 6;4-[2’-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]- 1,3-di- hydro -2H-Indol-2-one;4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-1,3-dihydroindol-2-one;4-[2-[[(4-Methylphenyl)sulfo;1,3-Dihydro-4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-;2H-Indol-2-one, 1,3-dihydro-4-[2-[[(4-Methylphenyl)sulfonyl]oxy]ethyl]-
• CAS NO: 139122-20-6
• Molecular Formula: C₁₇H₁₇NO₄S
• Molecular Weight: 331.39
• Product Categories: Pharmaceutical material and intermeidates;Aromatics;Indole Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 139122-20-6.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 561.181 °C at 760 mmHg
• Flash Point: 293.192 °C
• Appearance: /
• Density: 1.311
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Methanol
• PKA: 14.02±0.20(Predicted)
• CAS DataBase Reference: 4-[2'-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-1,3-DIHYDRO-2H-INDOLE-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[2'-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-1,3-DIHYDRO-2H-INDOLE-2-ONE(139122-20-6)
• EPA Substance Registry System: 4-[2'-[[(4-METHYLPHENYL)SULFONYL]OXY]ETHYL]-1,3-DIHYDRO-2H-INDOLE-2-ONE(139122-20-6)

Safety Data

• Hazardous Substances Data: 139122-20-6(Hazardous Substances Data)

Usage

Chemical Properties

Greenish Yellow Solid

Upstream product

• 139122-16-0 benzoic acid (2-(2-nitroethenyl))phenethyl ester 
• 1426679-27-7 2-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]acetic acid 
• 1441070-77-4 ethyl 3-[2-[2-(benzyloxy)ethyl]-6-nitrophenyl]-2-oxopropanoate 
• 1426679-26-6 1-[(2-methyl-3-nitrophenethyloxy)methyl]benzene 
• 855382-76-2 2-(2-methyl-3-nitrophenyl)ethyl alcohol 
• 23876-15-5 2-(3-nitro-2-methylphenyl)acetic acid 
• 139122-17-1 4-[2-(benzoyloxy)ethyl]-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 139122-18-2 4-(2-benzoyloxyethyl)-1,3-dihydro-2H-indolin-2-one 
• 168476-57-1 4-(2-acetoxyethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 139122-15-9 benzoic acid (2-formyl)phenethyl ester 
• 168476-58-2 2-[2-(chloromethyl)phenyl]ethylbenzoate 
• 168476-61-7 4-(2-acetoxyethyl)-1,3-dihydro-2H-indolin-2-one 
• 120427-95-4 4-(2-bromoethyl)-3-chloro-1,3-dihydro-2H-indolin-2-one 
• 120427-94-3 2-(2-bromoethyl)-β-nitrostyrene 

Downstream Products

• 91374-20-8 ropinirole hydrochloride 

Relevant articles and documents

Method for preparing ropinirole hydrochloride

The invention belongs to the technical field of medicinal chemistry and organic chemistry, and particularly relates to a method for preparing ropinirole hydrochloride. A novel compound 4 is synthesized by the aid of the method and is used as a raw material for preparing the ropinirole hydrochloride. The particular method includes dissolving the compound 4 in one or a plurality of types of ethyl alcohol/methanol/ethyl acetate to obtain liquid, adding Pd/C into the ethyl alcohol/methanol/ethyl acetate, and carrying out reaction to obtain compounds 5; dissolving the compounds 5, p-toluenesulfonylchloride and pyridine in one or a plurality of types of dichloromethane/trichloromethane/1, 2-dichloroethane/pyridine, and carrying out reaction to obtain compounds 6; dissolving the compounds 6, NaIand dipropyl amine in one or a plurality of types of DMF (dimethyl formamide)/DMSO (dimethylsulfoxide)/Toluene, and carrying out reaction to obtain ropinirole; dissolving the ropinirole in 1, 4 dioxane with hydrochloric acid, and carrying out reduced-pressure compression to obtain the ropinirole hydrochloride. A proportion of the compounds 5 to the p-toluenesulfonyl chloride to the pyridine is equal to 1:1.2:1.2. A proportion of the compounds 6 to the NaI to the dipropyl amine is equal to 1:1:1.2. The novel method for preparing the ropinirole hydrochloride has the advantages that the method includes simple and convenient steps and can be practically put into production, and raw materials for the ropinirole hydrochloride are simple and are easily available.

Improved preparation method for ropinirole hydrochloride

The invention discloses an improved preparation method for ropinirole hydrochloride. The ropinirole hydrochloride is a compound shown in the formula I and is prepared through a series of reactions with 2-phenylethanol as a starting raw material. Compared with the prior art, according to the method, raw materials are cheap and easy to get, reaction conditions are mild, technological operation is easy, control is easy, the product is high in total yield and purity, and the method is suitable for industrial production.

Synthesis and pharmacological evaluation of dual acting ligands targeting the adenosine A2A and dopamine D2 receptors for the potential treatment of parkinsons disease

A relatively new strategy in drug discovery is the development of dual acting ligands. These molecules are potentially able to interact at two orthosteric binding sites of a heterodimer simultaneously, possibly resulting in enhanced subtype selectivity, higher affinity, enhanced or modified physiological response, and reduced reliance on multiple drug administration regimens. In this study, we have successfully synthesized a series of classical heterobivalent ligands as well as a series of more integrated and drug-like dual acting molecules, incorporating ropinirole as a dopamine D2 receptor agonist and ZM 241385 as an adenosine A2A receptor antagonist. The best compounds of our series maintained the potency of the original pharmacophores at both receptors (adenosine A2A and dopamine D2). In addition, the integrated dual acting ligands also showed promising results in preliminary blood-brain barrier permeability tests, whereas the classical heterobivalent ligands are potentially more suited as pharmacological tools.