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

Uses

Ethyl 1-(4-Methoxyphenyl)-6-(4-nitrophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate is an intermediate in the synthesis of Apixaban (A726700), a potent, direct, selective, and orally active inhibitor of coagulation factor Xa. It is a potential new oral coagulant that may be useful prevention of venous thromboembolism in total hip, knee replacement orthopedic surgery and stroke in treatment of patient with venous thromboembolic disorder or 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

• 100-28-7 4-Nitrophenyl isocyanate 
• 536760-29-9 3-chloro-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 473927-63-8 ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate 
• 545445-40-7 3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one 
• 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 
• 27143-07-3 ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate 
• 503615-03-0 3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 1039914-85-6 5-chloro-N-(4-nitrophenyl)pentanamide 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 4509-90-4 5-bromovaleroyl chloride 
• 100-01-6 4-nitro-aniline 
• 104-94-9 4-methoxy-aniline 
• 38560-30-4 1-(4-nitrophenyl)piperidine-2-one 

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.

Process for the preparation of apixaban

A crystalline Form N-1 of apixaban substantially free from one or more of: 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; 7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-1-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide; or methyl 1-(4-methoxyphenyl)-7-oxo-6-(4-(2-oxopiperidin-1-yl)phenyl)-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate, relative to apixaban by area percentage of HPLC and having a mean particle size equal to or greater than 100 μm.

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.