Awesome and Easy Science Experiments about Ethyl 2-chloro-6-benzothiazolecarboxylate

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Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.

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Thiazole | C3H8082NS – PubChem,
Thiazole | chemical compound | Britannica

Extracurricular laboratory:new discovery of Ethyl 2-chloro-6-benzothiazolecarboxylate

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Starting from the structure of thioperamide, a known H3-antagonist, a new series of compounds with a benzothiazole nucleus instead of the cyclohexylcarbothioamide moiety was synthesized. Various substituents, selected by experimental design, were introduced in position 6 of the benzothiazole nucleus, in order to change its physico-chemical characteristics. The lipophilicity of the synthesized compounds was measured by means of RP-HPLC, and their H3-receptor affinity was evaluated by competitive binding assays on rat cortex synaptosomes, with the labelled ligand N(alpha)-[3H]methylhistamine. A QSAR analysis was performed on the experimental data, using also substituent constants taken from the literature. The newly synthesized compounds showed lower H3-affinities than thioperamide; quantitative structure-activity relationships, described by models obtained with PLS and MRA techniques, were observed among benzothiazole derivatives. According to these relationships, any attempt to improve the potency of these compounds should involve the substitution of the benzothiazole moiety with less bulky and/or more flexible structures, which should also be less lipophilic and allow better electronic interactions with the binding site. 1-(Benzothiazol-2-yl)-4-[(1H)-imidazol-4-yl]piperidine represents a limit structure for H3-activity, since it seems impossible to improve its affinity by means of substitution in the studied position of the benzothiazole nucleus, as shown by predictions performed by a PLS model.

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Thiazole | C3H8083NS – PubChem,
Thiazole | chemical compound | Britannica

More research is needed about Ethyl 2-chloro-6-benzothiazolecarboxylate

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.78485-37-7, Name is Ethyl 2-chloro-6-benzothiazolecarboxylate, molecular formula is C10H8ClNO2S. In a Patent,once mentioned of 78485-37-7, Application In Synthesis of Ethyl 2-chloro-6-benzothiazolecarboxylate

Compounds of formula (I) are useful in treating conditions or disorders prevented by or ameliorated by histamine-3 receptor ligands. Also disclosed are pharmaceutical compositions of compounds of formula (I), methods for using such compounds and compositions, and a process for preparing the compounds.

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Thiazole | C3H8085NS – PubChem,
Thiazole | chemical compound | Britannica

Brief introduction of 78485-37-7

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The reaction rate of a catalyzed reaction is faster than the reaction rate of the uncatalyzed reaction at the same temperature.78485-37-7, Name is Ethyl 2-chloro-6-benzothiazolecarboxylate, molecular formula is C10H8ClNO2S. In a Patent£¬once mentioned of 78485-37-7, Recommanded Product: 78485-37-7

The present invention provides compounds of Formula (I), and pharmaceutically acceptable salts thereof, as well as pharmaceutical compositions comprising these compounds and methods of using these compounds to prevent or treat FXR-mediated or TGR5-mediated diseases or conditions.

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Thiazole | C3H8076NS – PubChem,
Thiazole | chemical compound | Britannica

Brief introduction of 78485-37-7

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78485-37-7,Ethyl 2-chloro-6-benzothiazolecarboxylate,as a common compound, the synthetic route is as follows.

78485-37-7, Ethyl 2-chloro-benzo[d]thiazole-6-carboxylate (362 mg, 1.5 mol)After acidification with hydrochloric acid and (2R,6S)-2,6-dimethylpiperidin-4-one (127 mg, 1.0 mmol)Dissolved in isopropanol (30 mL), reacted at 100 C for 12 hours, concentrated,Purified by silica gel column chromatography (petroleum ether: ethyl acetate = 3:1).The title compound (80 mg, yield: 24.1%) was obtained.

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Reference£º
Patent; Hainan Xuanzhu Pharmaceutical Technology Co., Ltd.; Shi Chengkong; Chen Bo; (23 pag.)CN109320509; (2019); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

Brief introduction of 78485-37-7

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.78485-37-7,Ethyl 2-chloro-6-benzothiazolecarboxylate,as a common compound, the synthetic route is as follows.

To ethyl 2-chlorobenzo[d]thiazole-6-carboxylate (1d-1) (305 mg, 1.263 mmol) and (1R,3R,5S)-N-((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methyl)-8-azabicyclo[3.2.1]octan-3-amine hydrochloride (1c-1) (430 mg, 0.842 mmol, ?84% by weight) in DMA (5 ml) was added cesium carbonate (686 mg, 2.105 mmol). The resulting mixture was heated up to 60 C. for 16 h, cooled down to room temperature. The mixture was diluted with ethyl acetate, washed with water (4*), brine, dried, filtered, and concentrated. The residue was chromatographed by CombiFlash eluting with hexane to 70% ethyl acetate/hexane to give ethyl 2-((1R,3R,5S)-3-(((5-cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methyl)amino)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate (Example 1) (198 mg). LC/MS observed [M+H], 597.15.

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Reference£º
Patent; Enanta Pharmaceuticals, Inc.; Ma, Jun; Wang, Guoqiang; Wang, Bin; Xing, Xuechao; Shen, Ruichao; He, Jing; Or, Yat Sun; (530 pag.)US2018/99957; (2018); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica