536759-91-8

Basic information

• Product Name: 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
• Synonyms: 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester;ethyl 1-(4-Methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate;4,5,6,7-Tetrahydro-1-(4-Methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxyl;Ethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3;1H-Pyrazolo[3,4-c]pyridine-3-carboxylicacid,4,5,6,7-tetrahydro-1-(4-Methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-,ethylester;Apixaban iMpurityG;Apixaban impurity BMS-589154;4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl este
• CAS NO: 536759-91-8
• Molecular Formula: C22H20N4O6
• Molecular Weight: 436.4174
• EINECS: 1308068-626-2
• Mol File: 536759-91-8.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 658.75 °C at 760 mmHg
• Flash Point: 352.199 °C
• Appearance: /
• Density: 1.40
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.661
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: -3.80±0.20(Predicted)
• CAS DataBase Reference: 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(536759-91-8)
• EPA Substance Registry System: 4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester(536759-91-8)

Safety Data

• Hazardous Substances Data: 536759-91-8(Hazardous Substances Data)

Usage

Description

4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester is a complex organic compound that serves as an intermediate in the synthesis of various pharmaceuticals. It is characterized by its unique molecular structure, which includes a pyrazolo[3,4-c]pyridine core, a 4-methoxyphenyl group, a 4-nitrophenyl group, and an ester functional group.

Uses

Used in Pharmaceutical Industry:
4,5,6,7-Tetrahydro-1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester is used as an intermediate in the synthesis of Apixaban (A726700) for the following reasons:
1. Apixaban is a potent, direct, selective, and orally active inhibitor of coagulation factor Xa, which plays a crucial role in the blood clotting process. By inhibiting factor Xa, Apixaban helps prevent the formation of blood clots, reducing the risk of venous thromboembolism.
2. It is a potential new oral coagulant that may be useful in the prevention of venous thromboembolism in patients undergoing total hip or knee replacement orthopedic surgery. This application is significant as it offers an alternative to traditional anticoagulants, which may have more side effects and require frequent blood monitoring.
3. Apixaban is also used in the treatment of patients with venous thromboembolic disorder or with atrial fibrillation, a condition characterized by an irregular and often rapid heart rate. By reducing the risk of blood clot formation, Apixaban helps prevent stroke and other complications associated with atrial fibrillation.

InChI:InChI=1/C22H20N4O6/c1-3-32-22(28)19-18-12-13-24(14-4-6-16(7-5-14)26(29)30)21(27)20(18)25(23-19)15-8-10-17(31-2)11-9-15/h4-11H,3,12-13H2,1-2H3

Upstream product

• 503615-03-0 3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 473927-63-8 ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate 
• 536760-29-9 3-chloro-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 881386-01-2 3,3-dichloro-1-(4-nitrophenyl)piperidine-2-one 
• 38560-30-4 1-(4-nitrophenyl)piperidine-2-one 
• 104-94-9 4-methoxy-aniline 
• 100-01-6 4-nitro-aniline 
• 4509-90-4 5-bromovaleroyl chloride 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 1039914-85-6 5-chloro-N-(4-nitrophenyl)pentanamide 
• 100-28-7 4-Nitrophenyl isocyanate 
• 27143-07-3 ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate 
• 503614-56-0 1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3, 4-c]pyridine-3-carboxylic acid ethyl ester 
• 350-46-9 4-Fluoronitrobenzene 

Relevant articles and documents

PROCESS FOR PREPARING APIXABAN

The present invention relates to process for preparing apixaban, in particular polymorphic form N-1 thereof, as well as to a method for the preparation of crystalline apixaban, especially apixaban polymorphic form N-1.

Apixaban derivatives as well as preparation method and application thereof

The invention belongs to the technical field of medicines and discloses apixaban derivatives and analogues as well as a preparation method and application thereof. The structure of the compounds is shown as the following formula. Cheap and readily available paranitroaniline serves as an initial raw material. The preparation method comprises the following steps: performing amidation-cyclization, chlorination, condensation-elimination, cyclization-elimination, reduction, amidation-cyclization so as to obtain a key intermediate; and dehydrating, performing ammonolysis or chlorination, and condensing to synthesize the target compound. The method is simple in operation, convenient in after-treatment and high in yield. The in-vitro anti-coagulant activity of the target compound is investigated by determining the activated partial thromboplastin time (APTT) and thromboplastin time (PT). The EC2X(APTT) of result compounds APX-02, APX-15 and APX-16 is respectively 2.15mug/L, 3.65mug/L and 2.35mug/L, the EC2X(PT) of the result compounds is respectively 0.12mug/L, 3.57mug/L and 1.57mug/L, which are higher than the EC2X(APTT) value of 3.78mug/L and the EC2X(PT) value of 1.59mug/L of a positive control agent Apixaban. The compounds have high anti-coagulant activities. The EC2X(APTT) value of the rest compounds is between 5mug/L and 65mug/L, and the EC2X(PT) value is between 3mug/L and 18mug/L. The structural formula is as shown in the specification.

A precursor [...] the synthetic method of the compound of

The invention discloses a synthetic method of a novel apixaban precursor compound. The synthetic method comprises the following steps: the apixaban precursor compound (5) (shown in the specification) is subjected to cyclization to obtain the lactam target product apixaban precursor compound I (shown in the specification). According to the invention, the apixaban precursor compound (5) is adopted to prepare ethyl 1-(4-methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate, the yield can reach 87%, and in the entire synthetic route, the lowest yield of each step can reach over 80%, the total yield can reach about 49%, and valuable catalysts or reagents polluting the environment seriously are not used in the entire process.