78441-62-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole is used as a Nizatidine intermediate for the synthesis of Nizatidine, a histamine H2 receptor antagonist. Nizatidine is widely used in the treatment of conditions such as peptic ulcers, gastroesophageal reflux disease (GERD), and other acid-related disorders. As an intermediate, 2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole contributes to the development and production of effective medications for various gastrointestinal issues.
Chemical Properties:
2-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazole is described as a brown liquid, which is an important characteristic for its identification and handling in the laboratory and industrial settings. Understanding its physical properties aids in the safe and efficient processing of the compound during the synthesis of Nizatidine.

InChI:InChI=1/C9H17N3S2/c1-12(2)5-9-11-8(7-14-9)6-13-4-3-10/h7H,3-6,10H2,1-2H3

Upstream product

• 156-57-0 2-mercaptoethylamine hydrochloride 
• 78441-69-7 2-dimethylaminomethyl-4-hydroxymethylthiazole 
• 140176-73-4 4-chloromethyl-2-dimethylaminomethylthiazole 
• 92759-37-0 4-Hydroxy-4-(chloromethyl)-2-<(dimethylamino)methyl>thiazoline 
• 82586-71-8 2-dimethylaminomethyl-4-thiazolylmethylchloride hydrochloride 
• 82586-66-1 ethyl 2-(dimethylaminomethyl)-4-thiazolecarboxylate 

Downstream Products

• 82586-81-0 N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylurea 
• 87767-28-0 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methoxy-4-pyrimidone 
• 82586-82-1 N-methyl-N'-2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl-N-p-tolylsulfonylguanidine 
• 82586-82-1 N-methyl-N'-2-([2-(dimethylaminomethyl)-4-thiazolyl]methylthio)ethyl-N-p-tolylsulfonylguanidine 
• 76963-41-2 nizatidine 
• 106467-09-8 N-Benzoyl-N'-[2-(2-dimethylaminomethyl-thiazol-4-ylmethylsulfanyl)-ethyl]-N''-[3-(1H-imidazol-4-yl)-propyl]-guanidine 
• 112758-49-3 1-Benzoyl-3-[2-(2-dimethylaminomethyl-thiazol-4-ylmethylsulfanyl)-ethyl]-2-phenyl-isourea 

Relevant academic research and scientific papers

Preparation method of nizatidine bulk drug

The invention discloses a preparation method of a nizatidine bulk drug. The preparation method comprises the following steps: (1) preparing 2-(N,N-dimethylamino)-4-chloromethyl-4-hydroxy-4,5-dihydrothiazole (III); (2) preparing 2-(N,N-dimethylamino)-4-thiazolemethanol (IV); (3) preparing 2-(dimethylaminomethyl)-4-(2-aminoethylthiomethyl) thiazole (V); and (4) preparing nizatidine. The preparation method has the beneficial effects that the cost is low, the preparation process is simple, the yield is high, and the prepared nizatidine is high in purity.

AN IMPROVED PROCESS FOR PREPARING NIZATIDINE INTERMEDIATE

The present invention comprises: preparation of dimethylaminothioacetamide by a novel process and its conversion to pure 4-chloromethyl-4-hydroxy-2-dimethylaminomethyl-2-thiazoline by an improved process. The 4-chloromethyl-4-hydroxy-2-dimethylaminomethyl-2-thiazoline obtained by the present invention is substantially of good purity, capable of being used to product commercial quantities of Nizatidine pharmaceutical grade. Dimethylaminothioacetamide is prepared by reacting dimethylaminoacetonitrile with phosphorus pentasulfide, which is then reacted with 1,3-dichloroacetone in dialkylethers, to get substantially pure 4-chloromethyl-4-hydroxy-2-dimethylaminomethyl-2-thiazoline.

HISTAMINE H2-ANTAGONISTS

Histamine H 2-antagonists of the formula STR1 wherein p is 1 or 2; R 1 is hydroxy, amino, substituted amino or a 5-to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2, n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.

C-2 basically substituted thiazoles with H2-antagonistic activity/21st Comm.: H2-antihistamines

In studies on structure-activity relationships of histamine H2-receptor antagonists, C-2 basically substituted thiazoles were prepared and tested for their H2-antihistaminic activity on the isolated guinea-pig atrium and on the histamine stimulated acid secretion of the anaesthetized rat. As a basic substituent the dimethylaminomethyl group is especially suitable, while cyclic guanidines lead to lower H2-antagonistic activity.

THIADIAZOLE HISTAMINE H2-ANTAGONISTS

Histamine H 2-antagonists of the formula STR1 wherein p is 1 or 2; R 1 is hydroxy, amino, substituted amino or a 5-to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.

2-[2-(2-AMINOALKYL-4-THIAZOLYLMETHYLTHIO)ALKYL]-AMINO-5-SUBSTITUTED-4-PYRIMIDONES

2-2-(2-aminoalkyl-4-thiazolylmethylthio)-alkylene!amino-5-aromatic-substitute d alkylene-4-pyrimidones and related compounds, H. sub.2 receptor antagonists, useful in inhibiting gastric acid secretion in mammals.

Synthesis of thiazoles

Certain 4-halomethylthiazoles having a 2-substituted-aminomethyl group are prepared by reacting an aminothioamide with a dihalopropanone in the presence of a haloalkane and a bicarbonate, and dehydrating the resulting intermediate.

CHEMICAL COMPOUNDS

Histamine H 2-antagonists of the formula STR1 wherein p is 1 or 2; R 1 is hydroxy, amino, substituted amino or a 5-to 9-membered fully saturated nitrogen-containing heterocyclic ring attached via its nitrogen atom; m is an integer of from 0 to 2; n is an integer of from 2 to 4; Z is sulfur, oxygen or methylene; and A is an optionally substituted phenyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, thiadiazolyl, oxadiazolyl, furyl, thienyl or pyridyl ring; and nontoxic pharmaceutically acceptable salts, hydrates, solvates or N-oxides thereof are novel anti-ulcer agents. Intermediates and processes for their preparation are disclosed.