156274-32-7

Basic information

• Product Name: METHYL 3-AMINO-4-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE
• Synonyms: METHYL 3-AMINO-4-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE
• CAS NO: 156274-32-7
• Molecular Formula: C₁₂H₁₀FNO₂S
• Molecular Weight: 251.28
• Mol File: 156274-32-7.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL 3-AMINO-4-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 3-AMINO-4-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE(156274-32-7)
• EPA Substance Registry System: METHYL 3-AMINO-4-(4-FLUOROPHENYL)THIOPHENE-2-CARBOXYLATE(156274-32-7)

Safety Data

• Hazardous Substances Data: 156274-32-7(Hazardous Substances Data)

Upstream product

• 161833-42-7 3-amino-4-bromo-2-thiophenecarboxylic acid methyl ester 
• 1765-93-1 4-fluoroboronic acid 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 450-28-2 C₁₀H₈FNO 
• 2365-48-2 Methyl thioglycolate 
• 398-42-5 2-formyl-2-(4-fluorophenyl) acetonitrile 
• 459-22-3 4-fluorophenylacetonitrile 

Downstream Products

• 1027055-06-6 4-(4-Fluoro-phenyl)-3-ureido-thiophene-2-carboxylic acid ethyl ester 
• 160139-90-2 7-(4-fluorophenyl)thieno<3,2-d>pyrimidine-2,4-dione 
• 1621967-31-4 7-(4-fluorophenyl)-3-(4-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one 
• 1026704-20-0 Acetic acid 2-[7-(4-fluoro-phenyl)-2,4-dioxo-3,4-dihydro-2H-thieno[3,2-d]pyrimidin-1-ylmethoxy]-ethyl ester 
• 1027183-54-5 7-(4-Fluoro-phenyl)-2,4-bis-trimethylsilanyloxy-thieno[3,2-d]pyrimidine 
• 156274-13-4 4-para-fluorophenyl-3-(1-pyrrolyl)-2-thiophene-N-pyrrolidinocarboxamide 

Relevant articles and documents

Novel Solid-phase and solution-phase synthetic methods for trisubstituted Thieno[3,2-d]pyrimidine derivatives

The coupling of 7-aryl-3,4-dihydro-4-oxothieno[3,2-d]pyrimidine-2-carboxylic acid with a primary alkylamineloaded acid-sensitive methoxy benzaldehyde (AMEBA) resin, a benzotriazol-1-yloxytris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated amination reaction, and cleavage from the solid support yielded N-alkyl-4-(alkylamino)-7-arylthieno[3,2-d]pyrimidine-2-carboxamide derivatives. The progress of the reactions on solid phase was monitored through attenuated total reflectance-FTIR spectroscopy and was compared with representative solution-phase surrogates. Additionally, N-acylation (acid chloride, InF3 , CH3 CN, room temperature) and cyclization (DBN, 1,4-dioxane, 80 ° C) of a 3-amino-4-(4-t-butoxycarbonylphenyl) thiophene-2-carboxamide intermediate under previously unreported conditions provided 2-substituted thieno[3,2-d]pyrimidin-4(3H)-one derivatives, which were subsequently converted to 2-substituted 4-alkylamino-7-[4-(alkylaminocarbonyl)phenyl]thieno[3,2-d]pyrimidine derivatives through a reaction sequence consisting of a BOP-mediated amination reaction, t-butyl deprotection, and amide formation.

Novel thienopyrimidinones as mGluR1 antagonists

There has been much attention to discover mGluR1 antagonists for treating various central nervous system diseases such as seizures and neuropathic pain. Thienopyrimidinone derivatives were designed, synthesized, and biologically evaluated against mGluR1. Among the synthesized compounds, 3-(4-methoxyphenyl)- 7-(o-tolyl)thienopyrimidin-4-one 30 exhibited the most potent inhibitory activity with an IC50 value of 45 nM and good selectivity over mGluR5. Also, the selective mGluR1 antagonist 30 showed marginal hERG channel activity (IC50 = 9.87 μM), good profiles to CYP isozymes, and a good pharmacokinetic profile. Overall, the compound 30 was identified as a selective mGluR1 antagonist with a good pharmacokinetic profile, which is probably devoid of cardiac side effect and drug-drug interactions. Therefore, the compound 30 can be expected to be broadly used as mGluR1 antagonistic chemical probe in in vitro and in vivo study for investigating CNS diseases.