1039914-85-6

Basic information

• Product Name: 5-chloro-N-(4-nitrophenyl)pentanamide
• Synonyms: 5-chloro-N-(4-nitrophenyl)pentanamide;PentanaMide, 5-chloro-N-(4-nitrophenyl)-
• CAS NO: 1039914-85-6
• Molecular Formula: C₁₁H₁₃ClN₂O₃
• Molecular Weight: 257
• Mol File: 1039914-85-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 121-123℃
• Boiling Point: 476.3±30.0 °C(Predicted)
• Appearance: /
• Density: 1.314
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 13.70±0.70(Predicted)
• CAS DataBase Reference: 5-chloro-N-(4-nitrophenyl)pentanamide(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-N-(4-nitrophenyl)pentanamide(1039914-85-6)
• EPA Substance Registry System: 5-chloro-N-(4-nitrophenyl)pentanamide(1039914-85-6)

Safety Data

• Hazardous Substances Data: 1039914-85-6(Hazardous Substances Data)

Usage

Description

5-chloro-N-(4-nitrophenyl)pentanamide is an organic compound that serves as a key intermediate in the synthesis of various pharmaceuticals. It is characterized by the presence of a chloro and nitro group attached to a pentanamide backbone, which contributes to its reactivity and potential applications in medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
5-chloro-N-(4-nitrophenyl)pentanamide is used as a chemical intermediate for the preparation of Apixaban and its derivatives. Apixaban is an oral anticoagulant medication used to treat and prevent blood clots, making this intermediate crucial for the development and production of life-saving medications.
In the process for the preparation of Apixaban and intermediates thereof, 5-chloro-N-(4-nitrophenyl)pentanamide plays a vital role in the synthesis pathway, ensuring the efficient production of the desired active pharmaceutical ingredient (API). Its unique structural features facilitate specific chemical reactions that are essential for the formation of the final drug product.

Upstream product

• 1575-61-7 5-Chlorovaleroyl chloride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 1191091-32-3 N-(4-nitrophenyl)-5-(pyrrolidin-1-yl)pentanamide 
• 66242-24-8 N-(4-nitrophenyl)pentamethylenediamine 
• 1286232-23-2 4-azido-N-(4-nitrophenyl)valeramide 
• 503614-92-4 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxopiperidin-1-yl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid 
• 503612-86-0 1-(4-methoxyphenyl)-3-(1-methyl-4,5-dihydro-1H-imidazol-2-yl)-6-(4-(2-oxopiperidin-1-yl)phenyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one 

Relevant articles and documents

Alternate synthesis of apixaban (BMS-562247), an inhibitor of blood coagulation factor Xa

An alternate approach to apixaban was described. The synthesis features a novel and cost-effective synthetic strategy to construct a key N-phenylvalerolactam intermediate 4 from 4-nitroaniline. In addition, the modified synthetic route avoids the use of expensive reagents and significantly improves reaction yields. As demonstrated practically, apixaban was successfully synthesized in overall good yield (35%). Copyright Taylor & Francis Group, LLC.

Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity

A series of novel tetrahydropyrazolopyridone derivatives containing 1,3,4-triazole, triazolylmethyl, and partially saturated heterocyclic moieties as P2 binding element was designed, synthesized, and evaluated in vitro for anticoagulant activity in human and rabbit plasma. All compounds showed moderate to significant potency, and compounds 15b, 15c, 20b, 20c, and 22b were further examined for their inhibitory activity against human FXa in vitro. While compounds 15c and 22b were tested for rat venous thrombosis in vivo. The most promising compound 15c, with an IC50 (FXa) value of 0.14?μM and 98% inhibition rate, warranted further investigation as an FXa inhibitor.

A pyridine derivative

The present invention relates to the field of pharmaceutical chemistry, specifically to a class of compounds containing lactam and derivative thereof, and especially to a pyridine derivative as shown in general formula (I), preparation method and the use thereof as a Factor Xa inhibitor. The present invention further relates to the medical use of the compound and derivative thereof in preparation of anticoagulant drugs, particularly to the use in preparation of drugs for preventing or treating thrombosis or embolism.