22353-82-8

Basic information

• Product Name: 5-CHLORO-2-THIOPHENECARBOXAMIDE
• Synonyms: 5-CHLORO-2-THIOPHENECARBOXAMIDE;5-CHLOROTHIOPHENE-2-CARBOXAMID;5-Chlorothiophene-2-carboxamide;N-(5-chlorothiophen-2-yl)formamide
• CAS NO: 22353-82-8
• Molecular Formula: C₅H₄ClNOS
• Molecular Weight: 161.61
• Mol File: 22353-82-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 179-181°
• Boiling Point: 277.623 °C at 760 mmHg
• Flash Point: 121.702 °C
• Appearance: /
• Density: 1.475 g/cm³
• Vapor Pressure: 0.00447mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: 2-8°C
• PKA: 15.55±0.50(Predicted)
• CAS DataBase Reference: 5-CHLORO-2-THIOPHENECARBOXAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-CHLORO-2-THIOPHENECARBOXAMIDE(22353-82-8)
• EPA Substance Registry System: 5-CHLORO-2-THIOPHENECARBOXAMIDE(22353-82-8)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 22353-82-8(Hazardous Substances Data)

Usage

Description

5-CHLORO-2-THIOPHENECARBOXAMIDE is a chemical compound that serves as a metabolite of Rivaroxaban (R538000), a novel antithrombotic agent. It is characterized by its unique molecular structure, which includes a thiophene ring and a carboxamide functional group. 5-CHLORO-2-THIOPHENECARBOXAMIDE plays a significant role in the pharmacological activity of Rivaroxaban, contributing to its potent and selective inhibition of Factor Xa, a key enzyme in the coagulation cascade.

Uses

Used in Pharmaceutical Industry:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as an intermediate compound for the development of antithrombotic drugs, specifically for the synthesis of Rivaroxaban. Its role in the drug's mechanism of action is crucial, as it contributes to the highly potent and selective inhibition of Factor Xa, which is essential for the prevention and treatment of various thrombotic disorders.
Used in Cardiovascular Applications:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as a therapeutic agent for the prevention and treatment of thrombotic events, such as deep vein thrombosis, pulmonary embolism, and stroke. Its ability to selectively inhibit Factor Xa makes it a valuable tool in managing these conditions, as it helps to reduce the risk of clot formation without significantly increasing the risk of bleeding.
Used in Research and Development:
5-CHLORO-2-THIOPHENECARBOXAMIDE is used as a research compound for studying the pharmacological properties and mechanisms of action of Rivaroxaban and other direct Factor Xa inhibitors. This knowledge can be applied to the development of new antithrombotic agents with improved efficacy, safety, and selectivity.
Used in Drug Delivery Systems:
5-CHLORO-2-THIOPHENECARBOXAMIDE can be used in the development of novel drug delivery systems to improve the bioavailability, stability, and targeted delivery of Rivaroxaban and other antithrombotic agents. These systems may include nanoparticles, liposomes, or other advanced drug carriers designed to enhance the therapeutic potential of these compounds while minimizing potential side effects.

InChI:InChI=1/C5H4ClNOS/c6-4-2-1-3(9-4)5(7)8/h1-2H,(H2,7,8)

Upstream product

• 96-43-5 2-thienyl chloride 
• 463-72-9 carbamic chloride 
• 14345-95-0 (E)-N-[(5-chlorothiophen-2-yl)methylidene]hydroxylamine 
• 7283-96-7 5-Chloro-2-thiophenecarboxaldehyde 
• 125712-84-7 1-(5-chloro-thiophen-2-yl)-ethanol 
• 6310-09-4 2-acetyl-5-chlorothiophene 
• 35475-03-7 methyl 5-chloro-2-thiophenecarboxylate 
• 24065-33-6 5-Chlorothiophene-2-carboxylic acid 
• 42518-98-9 5-chlorothiophene-2-carbonyl chloride 

Downstream Products

• 58884-89-2 5-(5-chloro-2-thienyl)-1H-tetrazole 
• 366789-02-8 Rivaroxaban 
• 1312422-72-2 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide methanesulfonate 
• 1313610-83-1 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide thiocyanate 
• 1313610-84-2 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide phosphate 
• 1313610-85-3 5-chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-imidazol-4-yl)methyl)thiophene-2-carboxamide 1-hydroxy-2-naphthoate 
• 214759-22-5 C-(5-Chloro-thiophen-2-yl)-methylamine 

Relevant articles and documents

Heterocyclic compound and application thereof

The present disclosure relates to a heterocyclic compound represented by general formula I, a pharmaceutically acceptable salt, a stereoisomer, an enantiomer, a diastereoisomer, an atropisomer, an optical isomer, a raceme, a polymorphic substance, a solvate or an isotope labeled compound thereof, a pharmaceutical composition containing the heterocyclic compound, and a pharmaceutical use thereof. The heterocyclic compound disclosed by the invention is an immunomodulator, and particularly relates to an immunomodulator of a compound for activating STING.

A [...] intermediate 5 - chloro - N - (2 - oxirane ylmethyl) -2 - thiophene carboxamide preparation method

The invention provides a preparation method for a Rivaroxaban intermediate 5-chloro-N-(2-oxiranylmethyl)-2-thiophene methanamide. First, 5-chlorothiophene-2-formic acid and toluene are added into a reaction container, the temperature is risen to 80-85 DEG C slowly, then thionyl chloride is dripped slowly, and the temperature is risen to 95-105 DEG C; the reaction solution is cooled to 50-60 DEG C, equal-temperature reduced pressure distillation is carried out, the solvent is evaporated, and after toluene is added, a toluene solution of 5-chlorothiophene-2-formyl chloride is obtained; then propane is added in the toluene solution of 5-chlorothiophene-2- formyl chloride, then ammonia water is dripped under an ice-bath condition, and 5-chlorothiophene-2-methanamide is obtained; then 5-chlorothiophene-2-methanamide and potassium carbonate are added in a reaction container, then epoxy chloropropane is added, and after heating and stirring, 5-chloro-N-(2-oxiranylmethyl)-2-thiophene methanamide is obtained. In the technology route, reaction conditions are optimized, the reaction is mild, operation is simple, and the yield is high.

Rivaroxaban preparation method

The invention discloses a rivaroxaban preparation method and belongs to the field of medical chemistry. The method comprises the steps: firstly reacting N-(4-aminophenyl)-3-morpholinone with Boc anhydride or benzylcarbonyl chloride or other ester to generate N-(4-alkoxycarbonyl aminophenyl)-3-morpholinone intermediate I; reacting 5-chlorothiophene-2-methanamide with epoxy chloropropane to generate N-(1,2-glycidyl)-5-chlorothiophene-2-methanamide intermediate II. The intermediate I and the intermediate II are open loop-cyclization condensed under alkali condition to be directly prepared into rivaroxaban. The method has short synthesizing path, moderate condition, convenience to operate, high yield, stable product quality and easiness in achieving industrial production. The structural formula is shown in the specification.