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Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-(dimethylamino)-1,3-thiazole-5-carbaldehyde is used as a key intermediate in the synthesis of imidazo[4,5-b]pyridine derivatives. These derivatives have been found to be effective as modulators of anaplastic lymphoma kinase (ALK) and Janus kinase (JAK), which are important targets for the treatment of various proliferative disorders, including cancer and autoimmune diseases.
The compound's role in the preparation of these therapeutic agents is significant, as it contributes to the development of novel treatments that can potentially improve patient outcomes and address unmet medical needs.

InChI:InChI=1/C6H7ClN2OS/c1-9(2)6-8-5(7)4(3-10)11-6/h3H,1-2H3

Upstream product

• 4175-76-2 2,4-dichlorothiazole 
• 68-12-2 N,N-dimethyl-formamide 
• 92972-48-0 2,4-dichlorothiazole-5-carboxaldehyde 
• 124-40-3 dimethyl amine 

Downstream Products

• 877977-15-6 4-methoxy-2-dimethylamino-1,3-thiazole-5-carbaldehyde 
• 919016-61-8 C₈H₁₂N₂O₂S 
• 1242339-35-0 3-(4-chloro-2-dimethylamino-1,3-thiazol-5-yl)-1-phenyl-2-propen-1-one 

Relevant academic research and scientific papers

Discovery of thienothiazolocarboxamide analogues as novel anti-tubercular agent

In order to identify anti-tubercular agents with a novel scaffold, commercial libraries of small organic compounds were screened against a fluorescent strain of Mycobacterium tuberculosis H37Rv, using a dual phenotypic assay. Compounds were assessed again

Thiazole analogs of chalcones, capable of functionalization at the heterocyclic nucleus

The synthesis of new amino and alkoxy derivatives of thiazole-5- carbaldehyde, on the basis of which a,β-unsaturated ketones of the thiazole series were synthesized, are described in this paper. The possibility of obtaining chalcones and variation of substitution reactions in the thiazole ring has been shown. 2010 Springer Science+Business Media, Inc.

Azoles. Part 8. Metallation and Bromine -> Lithium Exchange Reactions of Polyhalogenothiazoles

2,4-Dichloro- and 2,4-dibromo-thiazole were deprotonated at position-5 with LiN(iPr)2 in THF at -78 deg C and the resulting lithium compound was quenched with various reagents, to yield various trisubstituted thiazoles. 2,5-Dibromo-4-chlorothiazole reacted with n-butyllithium in THF at -78 deg C at position-5 and the resulting lithium derivative gave 2-bromo-4-chloro-5-substituted thiazoles when quenched with the appropriate reagent.Both the 2- and 5-bromine-atoms were reactive in diethyl ether. 2,5-Dibromothiazole failed to deprotonate at position-4 under various reaction conditions, whereas treatment of 2,4,5-tribromothiazole with 1 mole equivalent of n-butyllithium in THF at -90 deg C, followed by addition of dimethyl disulfide after 30 min, gave a high yield of the 2,5-bis(methylthio)-compound.The tribromo-compound was also treated with 1 mole equivalent of n-butyllithium or methyllithium under various reaction conditions and the products formed after hydrolysis were analysed by 1H NMR spectroscopy.The 5-bromine-atom is the most reactive and greater selectivity is obtained with methyllithium.

An Easy General Synthesis of 2-(N,N-Dialkylamino)thiazol-5-yl Aldehydes and Ketones

Reaction between 2-chloro-5-thiazolyl-lithium and N,N-dialkylformamides or amides gave 2-N,N-dialkylaminothiazol-5-yl aldehydes or ketones on quenching with water.Quenching with acid gave 2-chlorothiazole-5-yl aldehydes or ketones, from which chloride was easily displaced by free amines.