79128-68-0

Basic information

• Product Name: 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester
• Synonyms: 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester;Methyl 3-(2,2,2-trifluoroacetaMido)thiophene-2-carboxylate;3-(N-TrifluoroacetylaMino)thiophene-2-carboxylic acid Methyl ester;2-Thiophenecarboxylic acid, 3-[(2,2,2-trifluoroacetyl)amino]-, methyl ester;3-(N-Trifluoroacetylamino)thiophene-2-carboxylic acid methyl ester, 97.5%
• CAS NO: 79128-68-0
• Molecular Formula: C₈H₆F₃NO₃S
• Molecular Weight: 253.1983496
• EINECS: 201-215-5
• Mol File: 79128-68-0.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester(79128-68-0)
• EPA Substance Registry System: 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester(79128-68-0)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 79128-68-0(Hazardous Substances Data)

Usage

General Description

The chemical 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylicacidMethylester is a compound with a molecular formula of C8H6F3NO2S. It is an ester derivative of 3-(2,2,2-trifluoro-acetylaMino)-thiophene-2-carboxylic acid, containing a methyl group attached to the carboxylic acid functional group. This chemical compound is used in medicinal chemistry and pharmaceutical research as a building block in the synthesis of various biologically active molecules. Its specific properties and applications may vary based on its use in different chemical reactions and processes.

InChI:InChI=1S/C8H6F3NO3S/c1-15-6(13)5-4(2-3-16-5)12-7(14)8(9,10)11/h2-3H,1H3,(H,12,14)

Upstream product

• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 76-05-1 trifluoroacetic acid 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 852330-31-5 5-bromo-3-(2,2,2-trifluoracetamido)thiophene-2-carboxylic acid methyl ester 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 1027708-01-5 methyl 3-(trans-4-methylcyclohexylcarbonylamino)-5-iodothiophene-2-carboxylate 
• 942589-45-9 methyl 3-amino-5-iodo-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.

Discovery of GS-9669, a thumb site II non-nucleoside inhibitor of NS5B for the treatment of genotype 1 chronic hepatitis C infection

Investigation of thiophene-2-carboxylic acid HCV NS5B site II inhibitors, guided by measurement of cell culture medium binding, revealed the structure-activity relationships for intrinsic cellular potency. The pharmacokinetic profile was enhanced through incorporation of heterocyclic ethers on the N-alkyl substituent. Hydroxyl groups were incorporated to modulate protein binding. Intrinsic potency was further improved through enantiospecific introduction of an olefin in the N-acyl motif, resulting in the discovery of the phase 2 clinical candidate GS-9669. The unexpected activity of this compound against the clinically relevant NS5B M423T mutant, relative to the wild type, was shown to arise from both the N-alkyl substituent and the N-acyl group.

THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS

The present invention relates to a compound represented by the formula (I): wherein each symbol is as defined in the specification, or a salt thereof, or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer