1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Base Information

• Chemical Name: 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester
• CAS No.: 473927-64-9
• Molecular Formula: C22H20IN3O4
• Molecular Weight: 517.323
• Hs Code.: 2933990090
• Mol file: 473927-64-9.mol

Synonyms:Ethyl 6-(4-Iodophenyl)-1-(4-Methoxyphenyl)-7-Oxo-4,5,6,7-Tetrahydro-1H-Pyrazolo[3,4-C]Pyridine-3-Carboxylate

Chemical Property of 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

Chemical Property:

• Boiling Point: 649.4±55.0 °C(Predicted)
• PKA: -0.78±0.20(Predicted)
• PSA: 73.66000
• Density: 1.60
• LogP: 3.93010
• Storage Temp.: 2-8°C(protect from light)

Purity/Quality:

99% ^*data from raw suppliers

Ethyl6-(4-Iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethyl 6-(4-Iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate is an intermediate 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 Jdisorder or with atrial fibrillation.

Technology Process of 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

There total 17 articles about 1-(4-Methoxyphenyl)-6-(4-iodophenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 75.0%

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one (473927-69-4) + ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate (27143-07-3) → 1-(4-methoxy-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (473927-64-9)

Guidance literature:

With triethylamine; In ethyl acetate; at 0 ℃; for 2h; Inert atmosphere; Cooling with ice; Reflux;

Reference yield: 71.0%

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one (473927-69-4) + ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate (473927-63-8) → 1-(4-methoxy-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (473927-64-9)

Guidance literature:

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one; ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate; With triethylamine; In toluene; for 24h; Heating;

With trifluoroacetic acid; In dichloromethane; for 24h; Further stages.;

DOI:10.1021/jm070245n

Reference yield: 63.0%

1-(4-iodophenyl)-3-trimethylsilyloxy-5,6-dihydro-1H-pyridin-2-one (1415831-80-9) + ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate (27143-07-3) → 1-(4-methoxy-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (473927-64-9)

Guidance literature:

1-(4-iodophenyl)-3-trimethylsilyloxy-5,6-dihydro-1H-pyridin-2-one; ethyl 2-chloro-2-(2-(4-methoxyphenyl)hydrazono)acetate; With triethylamine; In ethyl acetate; at 0 ℃; Inert atmosphere; Reflux;

With hydrogenchloride; In water; ethyl acetate; at 0 - 20 ℃;

upstream raw materials:

1-(4-iodo-phenyl)-3-morpholin-4-yl-5,6-dihydro-1H-pyridin-2-one

ethyl (2Z)-chloro[2-(4-methoxyphenyl)hydrazinylidene]ethanoate

4-methoxy-aniline

1-(4-iodophenyl)-3-trimethylsilyloxy-5,6-dihydro-1H-pyridin-2-one

Downstream raw materials:

1-(4-methoxy-phenyl)-7-oxo-6-[4-(2-oxo-piperidin-1-yl)-phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

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

ethyl 1-(4-methoxyphenyl)-7-oxo-6-[4-(2-oxo-1(2H)-pyridinyl)phenyl]-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylate

1-(4-methoxyphenyl)-3-methyl-6-[4-(2-oxo-2H-pyridin-1-yl)phenyl]-1,4,5,6-tetrahydropyrazolo[3,4-c]pyridin-7-one

Refernces

• 1、 -. "NOVEL PROCESS FOR THE PREPARATION OF A LACTAM-CONTAINING COMPOUND". . . Retrieved 2015/12/08.
• 2、 -. "A PROCESS FOR THE PREPARATION OF APIXABAN AND ITS INTERMEDIATES". Page/Page column 10. . Retrieved 2015/11/27.