107818-55-3

Basic information

• Product Name: 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester
• Synonyms: 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester;methyl 3-amino-5-bromothiophene-2-carboxylate;5-Bromo-3-aminothiophene-2-carboxylic acid methyl ester;3-Amino-5-bromo-2-thiophenecarboxylic acid methyl ester
• CAS NO: 107818-55-3
• Molecular Formula: C₆H₆BrNO₂S
• Molecular Weight: 236
• Mol File: 107818-55-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 345.5±37.0 °C(Predicted)
• Appearance: /
• Density: 1.745±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 1.00±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester(107818-55-3)
• EPA Substance Registry System: 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester(107818-55-3)

Safety Data

• Hazardous Substances Data: 107818-55-3(Hazardous Substances Data)

Usage

General Description

3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester is a chemical compound with the molecular formula C7H7BrNO2S. It is a derivative of thiophene, which is a heterocyclic compound commonly used in pharmaceuticals and agrochemicals. 3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester contains a bromine atom and an amino group, making it potentially useful in organic synthesis and medicinal chemistry. The methyl ester group makes it a versatile building block for the synthesis of more complex molecules. The compound may have potential applications in the development of pharmaceutical drugs and other biologically active compounds.

InChI:InChI=1S/C6H6BrNO2S/c1-10-6(9)5-3(8)2-4(7)11-5/h2H,8H2,1H3

Upstream product

• 99839-45-9 methyl 5-bromo-3-nitrothiophene-2-carboxylate 
• 852330-31-5 5-bromo-3-(2,2,2-trifluoracetamido)thiophene-2-carboxylic acid methyl ester 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 79128-68-0 methyl 3-(2,2,2-trifluoroacetamido)thiophene-2-carboxylate 

Downstream Products

• 914780-67-9 5-bromo-3-(2,2-dimethyl-[1,3]dioxan-5-ylamino)-thiophene-2-carboxylic acid methyl ester 
• 852330-31-5 5-bromo-3-(2,2,2-trifluoracetamido)thiophene-2-carboxylic acid methyl ester 
• 1244028-17-8 3-amino-5-bromo-N-(4-methoxybenzyl)thiophene-2-carboxamide 
• 1276130-32-5 methyl 5-bromo-3-(4-methyl-benzylamino)-thiophene-2-carboxylate 
• 1312816-01-5 methyl 5-(4-hydroxymethylphenyl)-3-(4-methylbenzylamino)thiophene-2-carboxylate 
• 1309853-33-5 5-bromo-3-[(2,4-dichloro-benzoyl)-isopropyl-amino]-thiophene-2-carboxylic acid methyl ester 
• 1309853-34-6 3-[(2,4-dichlorobenzoyl)isopropylamino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid methyl ester 
• 1309852-77-4 3-[(2,4-dichlorobenzoyl)isopropylamino]-5-(3,3-dimethylbut-1-ynyl)thiophene-2-carboxylic acid 
• 1309853-52-8 sodium 3-[(2,4-dichloro-benzoyl)-isopropyl-amino]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylate 

Relevant articles and documents

Solid-phase synthetic method for N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives

Herein, we describe a solid-phase synthetic method for synthesizing N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The derivatives consist of the biologically active 6-phenylthieno[3,2-d]pyrimidine scaffold. The template mediated synthetic strategy involving Suzuki coupling reactions between methyl 3-amino-5-bromothiophene-2-carboxylate and arylboronic acids afforded methyl 3-amino-5-arylthiophene-2-carboxylates. Cyclocondensation reactions involving methyl 3-amino-5-arylthiophene-2-carboxylates and methyl cyanoformate afforded esters, that when subjected to hydrolysis reactions yielded 6-aryl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-carboxylic acids (template compounds). These carboxylic acid templates were coupled with primary alkylamine-loaded acid-sensitive methoxybenzaldehyde (AMEBA) resins. The amide coupling reactions were followed by direct amination reactions mediated by benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP). The compounds were subsequently cleaved from the solid support, purified using the reverse phase-high performance liquid chromatography technique (RP-HPLC), and passed through a strong anion exchange (SAX) resin pretreated with water to yield the N-alkyl-4-alkylamino-6-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The reaction conditions for the solid-phase transformations were optimized using a solution-phase model using 2,4-dimethoxybenzyl-protected isobutylamine as a reactant. 2,4-Dimethoxybenzyl-protected isobutylamine, and not AMEBA resin-loaded isobutylamine was used during the process. Substituent variation experiments were performed using 6-aryl-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-carboxylic acids and a variety of primary and secondary amine building blocks. Additionally, we could include the Suzuki coupling step in a modified solid-phase synthetic sequence.

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Disclosed herein are compounds of Formula (I) and pharmaceutically acceptable salts thereof. The compounds of Formula (I) are useful for activating uncoupling protein 1 (UCP1) dependent thermogenesis. Also disclosed herein are methods of treating obesity

Thienopyridone derivative, method for preparing the same and pharmaceutical composition comprising the same

The present invention relates to a thienopyridone derivative, a production method thereof, and a pharmaceutical composition comprising the same and, more particularly, to a novel thienopyridone derivative comprising various substituents, a production method thereof, and a pharmaceutical composition for preventing or treating cancer, comprising the same as active ingredient.COPYRIGHT KIPO 2017