185104-11-4

Basic information

• Product Name: N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride
• Synonyms: Acotiamide hydrochloride;N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride;N-[2-[Bisisopropylamino]-ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide HCl
• CAS NO: 185104-11-4
• Molecular Formula: C21H30N4O5S.HCl
• Molecular Weight: 487.01264
• EINECS: 203-105-6
• Mol File: 185104-11-4.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• CAS DataBase Reference: N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride(185104-11-4)
• EPA Substance Registry System: N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride(185104-11-4)

Safety Data

• Hazardous Substances Data: 185104-11-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride is used as a potential therapeutic agent for various medical conditions. Its specific application reason is yet to be fully elucidated, but its chemical structure suggests that it may have interactions with biological targets, such as enzymes or receptors, that could be relevant to the treatment of certain diseases.
Used in Research and Development:
In the field of research and development, N-[2-[Bis(1-methylethyl)amino]ethyl]-2-[(2-hydroxy-4,5-dimethoxybenzoyl)amino]-4-thiazolecarboxamide hydrochloride can be used as a starting material or a tool compound for the synthesis of new drugs or the study of biological processes. Its unique structure may provide insights into the design of more effective and targeted pharmaceuticals.

Biological Activity

Acotiamide hydrochloride is an orally active, selective and reversible acetylcholinesterase (AChE) inhibitor, with an IC50 of 1.79 μM. Acotiamide hydrochloride can enhance gastric contractility and accelerate delayed gastric emptying. Acotiamide hydrochloride has the potential for the research of functional dyspepsia involving gastric motility dysfunction and intestinal inflammatory.

Upstream product

• 610-90-2 2,4,5-trihydroxybenzoic acid 
• 28373-21-9 2-hydroxy-4,5-dimethoxybenzoic acid methyl ester 
• 121-05-1 N',N'-diisopropyl-ethane-1,2-diamine 
• 42833-66-9 2,4,5-trimethoxybenzoyl chloride 
• 490-64-2 asaronic acid 
• 61203-48-3 2-iodo-4,5-dimethoxybenzoic acid 
• 185106-16-5 Acotiamide 
• 877997-98-3 2-hydroxy-4,5-dimethoxybenzoic acid phenyl ester 
• 5722-93-0 2-hydroxy-4,5-dimethoxybenzoic acid 
• 67-63-0 isopropyl alcohol 

Relevant articles and documents

Preparation method of acotiamide hydrochloride impurity

The invention discloses a preparation method of an acotiamide hydrochloride impurity. The method comprises the following steps: carrying out acylating chlorination on a raw material 2,4,5-trimethoxybenzoic acid to obtain 2,4,5-trimethoxybenzoyl chloride, and carrying out an amidation reaction on the 2,4,5-trimethoxybenzoyl chloride and 2-amino-4-ethoxycarbonyl-1,3-thiazole to obtain 2-amino-4-ethoxycarbonyl-1,3-thiazole (intermediate 1); hydrolyzing the intermediate 1 with sodium hydroxide to obtain 2-[N-(2,4,5-trimethoxybenzoyl)amino]-4-carboxyl-1,3-thiazole (intermediate 2); and performing an acylating chlorination reaction on the intermediate 2 to obtain an acyl chloride group, performing an amidation reaction on the acyl chloride group and N,N-diisopropylethylenediamine to obtain N-[2-(diisopropylamino)ethyl]-2-[(2,4,5-trimethoxybenzoyl)amino]-4-thiazole formamide (acotiamide), and performing a salt forming reaction on the acotiamide to obtain acotiamide hydrochloride. The preparation method of the acotiamide hydrochloride impurity has the advantages of mild reaction conditions, simple operation, low cost and high yield, and is suitable for industrial production.

IMPROVED METHOD FOR MANUFACTURING ACOTIAMIDE

PROBLEM TO BE SOLVED: To provide a method for manufacturing acotiamide or acotiamide hydrochloride trihydrate capable of avoiding the use of 2,4,5-trimethoxy benzoyl chloride that is an intermediate manufactured by using thionyl chloride. SOLUTION: There is provided a method for manufacturing acotiamide or acotiamide hydrochloride trihydrate comprising the steps of: manufacturing 2-[(2,4,5-trimethoxy benzoyl) amino]-1,3-thiazole-4-ethyl carboxylate from 2,4,5-trimethoxy benzoic acid S- (benzothiazole-2-yl) and 2-amino-1,3-thiazole-4-ethyl carboxylate; manufacturing 2-[(2-hydroxy-4,5-dimethoxy benzoyl) amino]-1,3-thiazole-4-ethyl carboxylate by demethylation; and reacting the resultant product with N,N-diisopropyl ethylenediamine to manufacture acotiamide. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

Industrial production method of acotiamide hydrochloride

The invention discloses an industrial production method of acotiamide hydrochloride. The industrial production method comprises the following steps that firstly, 2,4,5-trimethoxy benzoic acid serves as an initial raw material, acylating chlorination is ca

A synthesis method of arab League tests for the amine hydrochloride

The invention relates to a synthetic method of acotiamide hydrochloride. The synthetic route of the acotiamide hydrochloride comprises the following steps: protecting hydroxyl vicinal to carboxyl in a formula (1) compound to obtain a formula (2) compound,

Acotiamide hydrochloride preparation method

The invention discloses an acotiamide hydrochloride preparation method. The acotiamide hydrochloride preparation method includes: taking 2,4,5-trihydroxybenzoic acid as a raw material easy to obtain, subjecting methyl iodide to selective methylation react

A hydrochloric acid trihydrate arab League tests for the amine method for the preparation of

The invention discloses a method for preparing an acotiamide hydrochloride trihydrate. The method comprises the following steps: 1, reacting a compound of a formula (1) and N,N-diisopropylethylamine (2) to obtain a compound (3); 2, performing two-site amino deprotection on the compound (3) to obtain a compound (4); 3, condensing the compound (4) and an acyl chloride derivative to obtain a compound (5); 4, further preparing the compound (5) to obtain the acotiamide hydrochloride trihydrate (6).

arab League tests for the amine and a method for the preparation of its hydrochloride (by machine translation)

The invention discloses a arab League tests for the amine method for preparing and its hydrochloride, 2 - [(2-hydroxy -4,5-dimethoxy-benzoyl) amino] - 1,3-thiazole-4-carboxylic acid methyl ester, and N, N-diisopropyl ethylenediamin in the molten state after reaction under N-[ 2 - (diisopropyl amino) ethyl] - 2 - [(2-hydroxy -4,5-dimethoxy-benzoyl) amino] - 1,3-thiazole-4-carboxamide, hydrochloric acid for hydrochloric acid prepared by adding dropwisely added methanol trihydrate arab League takes a test for somebody else the amine, the technical proposal of the present invention reduces the use of toluene, economic and convenient, the reaction is complete, process safety; reduced at the same time the residual toluene in the final product, and impurity 2 - [(2-hydroxy -4,5-dimethoxy-benzoyl) amino] - 4-carboxyl -1, the content of 3-thiazole, the product quality is promoted; and is easy to be refined and purification of the crude product, the reaction yield is high. (by machine translation)

arab League tests for the amine method of preparing hydrochloric acid

The invention discloses a method for preparing a compound of formula (5). The method comprises the following steps: 1, reacting a compound of formula (2) with triphosgene, diphosgene or phosgene in a non-polar solvent in the presence of an organic alkali to obtain a product, reacting the obtained product with a compound of formula (3) to obtain a compound of formula (1); and 2, reacting the compound of formula (1) with a compound of formula (6) in 1,4-dioxane to obtain a substance, reacting the substance with HCl to form a salt which is the compound of formula (5), wherein R in the compound of formula (3) and the compound of formula (5) is a methyl group or an ethyl group.

METHOD FOR PRODUCING 2-BROMO-4,5-DIALKOXY BENZOIC ACID

Provided is a method for effectively producing a 4,5-dialkoxy-2-hydroxybenzoic acid from an inexpensive raw material. A method for producing a 2-bromo-4,5-dialkoxybenzoic acid represented by the following formula (2): (wherein each of R1 and R2 represents a lower alkyl group), the method including causing a 3,4-dialkoxybenzoic acid represented by the following formula (1): (wherein R1 and R2 have the same meanings as defined above) to react with bromine in concentrated hydrochloric acid.

METHOD FOR PRODUCING AMINOTHIAZOLE DERIVATIVE AND PRODUCTION INTERMEDIATE

Disclosed is a selective demethylation process of a 2-methoxy group. Specifically disclosed is a method for producing a compound represented by the formula (7) below through the following reactions.