1086026-31-4

Basic information

• Product Name: 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one
• Synonyms: 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one;Dehydro Ivabradine;Dehydro Ivabradine (Ivabradine IVA-3 IMpurity);Dehydro Ivabradine Hydrochloride;Ivabradine Impurity a;Ivabradine impurity 1
• CAS NO: 1086026-31-4
• Molecular Formula: C₂₇H₃₄N₂O₅
• Molecular Weight: 466.56926
• EINECS: 200-111-5
• Product Categories: Amines;Aromatics;Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Aromatics, Chiral Reagents, Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1086026-31-4.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Storage Temp.: -86°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Temperature Sensitive
• CAS DataBase Reference: 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one(1086026-31-4)
• EPA Substance Registry System: 3-[3-[[[(7S)-3,4-DiMethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]Methyl]MethylaMino]propyl]-1,3-dihydro-7,8-diMethoxy-H-3-benzazepin-2-one(1086026-31-4)

Safety Data

• Hazardous Substances Data: 1086026-31-4(Hazardous Substances Data)

Usage

Uses

Dehydro Ivabradine is an impurity of Ivabradine (I940500)

Upstream product

• 73942-87-7 7,8-Dimethoxy-1,3-dihydro-2H-3-benzazepin-2-one 
• 866783-13-3 1-[(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl]-N-methylmethanamine hydrochloride 
• 85175-59-3 3-(3-chloropropyl)-1,3-dihydro-7,8-dimethoxy-2H-3-benzazepine-2-one 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 5663-56-9 2-(3,4-dimethoxyphenyl)acetamide 
• 866783-12-2 [{(7S)-3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-yl}methyl](methyl)amine 
• 73954-34-4 N-(2,2-dimethoxy-ethyl)-3,4-dimethoxyphenylacetamide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 37895-73-1 1,2-dibromo-4,5-dimethoxybenzene 
• 148870-57-9 7,8-dimethoxy-3-[3-iodopropane]-1,3-dihydro-2H-3-benzazepin-2-one 
• 91-16-7 1,2-dimethoxybenzene 
• 55171-76-1 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one 

Downstream Products

• 155974-00-8 ivabradine 
• 148849-67-6 ivabradine hydrochloride 

Relevant articles and documents

AN IMPROVED PROCESS FOR THE SYNTHESIS OF IVABRADINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

: Disclosed herein is an improved process for the preparation of Ivabradine and pharmaceutically acceptable salts thereof. The invention more particularly disclosesthe synthesis of key intermediates viz.,(S)-N-[(4,5-dimethoxybenzocydobut-l-yl)-methyl]-N- (methyl)amine hydrochloride of Formula-II and 3-(3-Iodopropyl)-7,8-dimethoxy-1,3-dihydro-2H-3-benzapin-2-one of Formula-III, and its use in industrial synthesis of Ivabradine and pharmaceutically acceptable salts thereof.

Dehydrogenated ivabradine oxalate preparation method

The invention relates to the technical field of organic chemical synthesis, in particular to a dehydrogenated ivabradine oxalate preparation method and aims to solve technical problems of high impurity content and complexity in subsequent treatment in a dehydrogenated ivabradine oxalate synthesis process. The technical scheme for implementation includes that a synthetic route includes: adding a compound (III) or salts thereof and a compound (II) into a nonpolar solvent, mixing, adding inorganic base, iodine compounds and a phase transfer catalyst, and heating for stirring reaction to obtain acompound (I); adding oxalic acid ethanol solution for salification, so that high-purity dehydrogenated ivabradine oxalate is obtained. The dehydrogenated ivabradine oxalate preparation method has advantages that impurity (A) content can be evidently reduced, reaction liquid purity can be remarkably improved while product yield is increased, an aftertreatment process is simplified, complicated operations of distillation or repeated extraction in use of polar solvents are avoided, and the method is more suitable for industrialization.

Ivabradine and its intermediate preparation method

The invention provides a preparation method for ivabradine and an intermediate thereof dehydrogenated ivabradine. The preparation method of the dehydrogenated ivabradine comprises: step a1, enabling a compound shown as a formula II and a compound shown as a formula III to have a nucleophilic substitution reaction in a polar aprotic solvent in the presence of an acid binding agent and a composite phase-transfer catalyst to generate dehydrogenated ivabradine; and step b1, performing separation and purification on dehydrogenated ivabradine obtained in the step a1. The composite phase-transfer catalyst is composed of a quaternary ammonium salt phase-transfer catalyst and a polyether phase-transfer catalyst with the mass ratio of 1-10:1, and X in the formula II is selected from Cl, Br, I, sulfonyloxy, methane sulfonyloxy, benzene sulfonyloxy, p-methylbenzene sulfonyloxy, o-methylbenzene sulfonyloxy or m-methylbenzene sulfonyloxy. The method is capable of substantially shortening the time of nucleophilic substitution reaction, improving product purity, avoiding a column chromatography process and reducing production cost.