129880-84-8

Usage

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2-(4-MORPHOLINO)-5-THIAZOLECARBOXALDEHYDE is used as a key intermediate in the synthesis of thiazole analogs of chalcones. These analogs are of significant interest due to their potential therapeutic properties, including anti-inflammatory, antimicrobial, and anticancer activities. The compound's unique structure allows for the development of novel drugs with improved efficacy and reduced side effects.
Used in Chemical Synthesis:
In the field of organic chemistry, 4-CHLORO-2-(4-MORPHOLINO)-5-THIAZOLECARBOXALDEHYDE serves as a valuable building block for the creation of more complex molecules. Its reactivity and functional groups make it a useful component in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
4-CHLORO-2-(4-MORPHOLINO)-5-THIAZOLECARBOXALDEHYDE is also utilized in research and development laboratories for the exploration of new chemical reactions and the development of innovative synthetic methods. Its unique properties make it an attractive candidate for studying reaction mechanisms and developing new strategies for the synthesis of complex molecules.

InChI:InChI=1/C8H9ClN2O2S/c9-7-6(5-12)14-8(10-7)11-1-3-13-4-2-11/h5H,1-4H2

Upstream product

• 4394-85-8 4-morpholinecarboxaldehyde 
• 4175-76-2 2,4-dichlorothiazole 
• 110-91-8 morpholine 
• 92972-48-0 2,4-dichlorothiazole-5-carboxaldehyde 
• 19983-32-5 2-(morpholin-4-yl)-1,3-thiazol-4-ol 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 919016-55-0 C₁₀H₁₄N₂O₃S 
• 1242339-46-3 C₁₇H₁₇ClN₂O₃S 
• 1242339-45-2 3-(4-chloro-2-morpholino-1,3-thiazol-5-yl)-1-(4-chlorophenyl)-2-propen-1-one 
• 1242339-42-9 C₁₆H₁₅ClN₂O₂S 

Relevant academic research and scientific papers

Preparation and characterisation of N-disubstituted 2-amino-4-chloro-5-formyl-thiazoles and their dicyanmethylene derivatives

In contrast to N-disubstituted 3-hydroxy-anilines 5 which react with the Vilsmeier reagent to N-substituted 4-amino-salicylaldehydes 7 their heteroanalogous N-disubstituted 2-amino-4-hydroxy-thiazoles 6 react with the same reagent to N-substituted 2-amino

Improved Synthesis of 2-Substituted 4-Chlorothiazole-5-carbaldehydes

An improved method for the reaction of 2,4-dichlorothiazole-5-carbaldehyde (2) with secondary amines was established using potassium carbonate in acetonitrile at room temperature instead of deprotonation with butyllithium in tetrahydrofuran at -78°. The m

Ultrasound promoted montmorillonite K-10 catalyzed synthesis, characterization, molecular modelling, SAR and hypoglycemic studies of new rhodanine bejeweled acridine analogues

In the present work an efficient ultrasound promoted synthesis of (Z)-2-((4-chloro-2-(piperidin/morpholin-1-yl)thiazol-5-yl)methylene)-3,3,7,9 tetra methyl-3,4-dihydroacridin-1 (2H) -one analogues 6(a-h) via Knoevenagel condensation using MK-10 catalyst have been reported. MK-10 due to its diverse properties and high surface area to volume ratio exhibits favorable features for the reaction response such as the shorter reaction time, simple work-up procedure, clean reaction profiles and excellent product yields through reusability of the catalyst upto five cycles. In silico molecular docking studies were carried out to find out the effective binding affinity of the synthesized acridine analogues towards PPARγ protein (Id-2XKW). The results obtained showed that compounds 6c and 6g possess good binding interaction towards PPARγ with binding energy of -9.6 and -9.0 k.cal/mol which was greater than standard Acarbose (-8.9 k.cal/mol) and comparable to that of standard pioglitazone (-9.8 k.cal/mol). In vitro α-amylase and α-glucosidase assays were performed for hypoglycemic activity evaluation. The compounds 6c and 6g at a concentration of 100 μg/mL showed 87.18 ± 0.90 and 83.34 ± 0.15 percent inhibition towards α-glucosidase, 85.24 ± 1.06 and 80.76 ± 0.55 percent inhibition towards α-amylase which was higher than standard pioglitazone and on par to that of Acarbose.

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

Efficient synthesis of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)- 4,5-dihydro-1h-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents

The α,β-unsaturated carbonyl compounds 5a-f were prepared by reaction between 2-chloro-4-morpholinothiazol-5-carbaldehyde 3 and substituted acetophenones 4a-f. Treatment of compounds 5a-f with hydrazine hydrate employing mild reaction conditions led to the formation of 4,5-dihydro-1H-pyrazoles 6a-f. Then the treatment with acetic anhydride or formic acid afforded the expected 4,5-dihydro-1H-pyrazoles 7a-f and 8a-f. The antifungal activity of each series of synthesized compounds was determined against the clinically important fungi Candida albicans and Cryptococcus neoformans. In addition, the most active compounds 7e and 7f were tested in combination with the commercial antifungal agents: fluconazole, itraconazole, and amphotericin B. Compound 7e showed a synergistic effect with fluconazole against C. albicans while 7f showed synergistic activities with all tested antifungal drugs against the same yeast.

Synthesis and antidiabetic activity of morpholinothiazolyl-2,4- thiazolidindione derivatives

We report the synthesis and the in vitro insulin releasing and glucose uptake activity of the morpholino thiazolyl-2,4-thiazolidinediones (1-15). Compounds 5, 1115 (at lower concentration; 0.001mg/ml) were able to increase insulin release in the presence

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.

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.