136539-01-0

Basic information

• Product Name: 4-Thiazolecarboxylicacid,2-amino-5-chloro-,ethylester(9CI)
• Synonyms: 4-Thiazolecarboxylicacid,2-amino-5-chloro-,ethylester(9CI);4-Thiazolecarboxylic acid, 2-aMino-5-chloro-, ethyl ester;2-Amino-5-chloro-4-thiazolecarboxylic acid ethyl ester;2-AMino-5-chloro-thiazole-4-carboxylic acid ethyl ester;ethyl 2-amino-5-chloro-1,3-thiazole-4-carboxylate
• CAS NO: 136539-01-0
• Molecular Formula: C₆H₇ClN₂O₂S
• Molecular Weight: 206.65
• Product Categories: THIAZOLE
• Mol File: 136539-01-0.mol

Chemical Properties

• Boiling Point: 343.3±22.0 °C(Predicted)
• Appearance: /
• Density: 1.468
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• PKA: 0.88±0.10(Predicted)
• CAS DataBase Reference: 4-Thiazolecarboxylicacid,2-amino-5-chloro-,ethylester(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Thiazolecarboxylicacid,2-amino-5-chloro-,ethylester(9CI)(136539-01-0)
• EPA Substance Registry System: 4-Thiazolecarboxylicacid,2-amino-5-chloro-,ethylester(9CI)(136539-01-0)

Safety Data

• Hazardous Substances Data: 136539-01-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-Thiazolecarboxylic acid, 2-amino-5-chloro-, ethyl ester (9CI) is used as a building block in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. Its unique structure and reactivity make it a valuable component in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 4-Thiazolecarboxylic acid, 2-amino-5-chloro-, ethyl ester (9CI) is utilized for the development of drugs. Its ability to modify biological activity and improve the properties of existing drug candidates makes it a promising compound for the creation of novel therapeutic agents.
Used in Research and Development:
4-Thiazolecarboxylic acid, 2-amino-5-chloro-, ethyl ester (9CI) is also employed in research and development in the field of materials science and other related industries. Its unique structure and reactivity contribute to the exploration of new materials and the advancement of scientific knowledge.
Used in Pharmaceutical Industry:
4-Thiazolecarboxylic acid, 2-amino-5-chloro-, ethyl ester (9CI) is used as a key intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs with improved efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical industry, 4-Thiazolecarboxylic acid, 2-amino-5-chloro-, ethyl ester (9CI) is utilized in the synthesis of agrochemicals, such as pesticides and herbicides, to enhance crop protection and yield.

Upstream product

• 5398-36-7 2-aminothiazole-4-carboxylate 
• 32955-21-8 2-amino-thiazole-5-carboxylic acid ethyl ester 

Downstream Products

• 425392-45-6 5-chlorothiazole-4-carboxylic acid ethyl ester 
• 425392-51-4 5-chloro-2-phenylethynyl-thiazole-4-carboxylic acid ethyl ester 
• 425392-47-8 5-chloro-2-(2-methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester 
• 425392-48-9 5-chloro-2-(4-methoxy-phenyl)-thiazole-4-carboxylic acid ethyl ester 
• 425392-44-5 2-bromo-5-chlorothiazole-4-carboxylic acid ethyl ester 
• 135925-33-6 Ethyl 2,5-dichloro-4-thiazolecarboxylate 

Relevant articles and documents

Rationally Designed Polypharmacology: α-Helix Mimetics as Dual Inhibitors of the Oncoproteins Mcl-1 and HDM2

Protein–protein interactions (PPIs), many of which are dominated by α-helical recognition domains, play key roles in many essential cellular processes, and the dysregulation of these interactions can cause detrimental effects. For instance, aberrant PPIs involving the Bcl-2 protein family can lead to several diseases including cancer, neurodegenerative diseases, and diabetes. Interactions between Bcl-2 pro-life proteins, such as Mcl-1, and pro-death proteins, such as Bim, regulate the intrinsic pathway of apoptosis. p53, a tumor-suppressor protein, also has a pivotal role in apoptosis and is negatively regulated by its E3 ubiquitin ligase HDM2. Both Mcl-1 and HDM2 are upregulated in numerous cancers, and, interestingly, there is crosstalk between both protein pathways. Recently, synergy has been observed between Mcl-1 and HDM2 inhibitors. Towards the development of new anticancer drugs, we herein describe a polypharmacology approach for the dual inhibition of Mcl-1 and HDM2 by employing three densely functionalized isoxazoles, pyrazoles, and thiazoles as mimetics of key α-helical domains of their partner proteins.

DUAL INHIBITORS OF THE BCL-2 AND HDM2 FAMILIES THROUGH CO-MIMICRY OF THE BH3 AND P53-ALPHA-HELICES

The invention relates to dual HDM2/Bcl-2 inhibitors, providing a synergistic effect to help promote apoptosis in tumorigenic cells.

ALKYNYL ALCOHOLS AND METHODS OF USE

The invention relates to compounds of formula (I), wherein Q, A1-A8, R4 and R5 are as described herein. Compounds of formula (I) and pharmaceutical compositions thereof are useful in the treatment of diseases and disorders in which undesired or over-activation of NF-kB signaling is observed.

THIAZOLE DERIVATIVES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

The present invention relates to thiazole derivatives of Formula (I) and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cere

SUBSTITUTED PIPERAZINES OF AZEPINES, OXAZEPINES, AND THIAZEPINES

Described herein are antipyschotic compounds of formula (I) wherein: is an optionally benzo-fused five or six member aromatic ring having zero to three hetero atoms independently selected from N, O, and S; R1 is hydrogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, or (C1-4) alkyl, wherein the (C1-4) alkyl is unsubstituted or substituted with hydroxy, methoxy, ethoxy, OCH2CH2OH, -CN, imidazolidin-2-one, phenyl, or tetrazole wherein tetrazole is unsubstituted or substituted with (C1-4) alkyl; R2 is H, halogen, (C1-6) fluoroalkyl, (C3-6) cycloalkyl, OR6, SR6, NO2, CN, COR6, C(O)OR6, C(OH)R6, CONR7R8, phenyl or (C1-6) alkyl, wherein the (C1-6) alkyl is unsubstituted or substituted with a hydroxy; R3 is hydrogen, (C 1-6)fluoroalkyl , (C3-6) cycloalkyl, (C2-6) alkenyl, phenyl, monocyclic heteroaromatic, bicyclic heteroaromatic, or (C1-4)alkyl wherein (C1-4) alkyl is unsubstituted or substituted with a phenyl; R4 and R5 are independently selected from hydrogen, halogen, (C1-6) alkyl, (C1-6) fluoroalkyl, OR9, SR9, NO2, CN, or COR9; R6 is hydrogen, (C1-6) fluoroalkyl, or (C1-6) alkyl; R7 and R8 are independently hydrogen, or (C1-6) alkyl; R9 is hydrogen, (C1-6) fluoroalkyl, (C1-6) alkyl; Alk is (C1-4) alkylene unsubstituted or substituted with a hydroxy; Y is oxygen, sulfur, SO2, or a bond; X is CH2, C=O, S, O, or SO2; Z is hydrogen, halogen, (C1-6) alkyl, (C1-6)fluoroalkyl, -OH, (C1-6) alkoxy, (C1-6) fluoroalkoxy, (C1-6) alkylthio, (C1-6) acyl, (C1-4)alkylsulfonyl, -OCF3, -NO2, - CN, carboxamido which may be substituted on the nitrogen by one or two (C1-4) alkyl groups, and -NH2 in which one of the hydrogens may be replaced by a (C1-4) alkyl group and the other hydrogen may be replaced by either a (C1-4) alkyl group, a (C1-6) acyl group, or a (C1-4) alkylsulfonyl group; the phenyl of R1, R2 or R3 is independently unsubstituted or substituted with one to three substituents independently selected from Z; the monocyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; the bicyclic heteroaromatic of R3 is unsubstituted or substituted with one to three substituents independently selected from Z; and salts, solvates, and crystal forms thereof. Also described are the use of the compounds of formula (I) as antagonists of the dopamine D2 receptor and as agents for the treatment of psychosis and bipolar disorders, and pharmaceutical formulations of the compounds of formula (I).

Regiocontrolled Synthesis of Substituted Thiazoles

(Formula Presented) The regiocontrolled synthesis of 2,5-disubstituted and 2,4,5-trisubstituted thiazoles from ethyl 2-bromo-5-chloro-4-thiazolecarboxylate 1 using sequential palladium-catalyzed coupling reactions is described.

Synthesis of 2,5-dihalothiazole-4-carboxylates

An efficient synthesis of 2,5-dihalothiazole-4-carboxylates has been described. Halogenation of aminothiazole carboxylate with NBS or NCS and subsequent diazotization with isoamyl nitrite and halogenation with CuBr2, CuCl2 or CH2I2 provided the corresponding diahalothiazole derivatives. The four-step process described is amenable to scale-up and requires no chromatographic purification in all the steps.

Synthesis and Reactions of Halogenated Thiazole Isocyanates

A synthesis of 2-chloro-4-(trifluoromethyl)-5-isocyanatothiazole and 2,5-dichloro-5-isocyanatothiazole is described via the "Curtius Rearrangement" performed under anhydrous conditions.The synthetic procedure described allows for the isolation, storage, a