5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide

Base Information

• Chemical Name: 5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide
• CAS No.: 1643330-62-4
• Molecular Formula: C₂₀H₂₆ClN₃O₃
• Molecular Weight: 391.898
• Mol file: 1643330-62-4.mol

Synonyms:

Chemical Property of 5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide

Chemical Property:

• Boiling Point: 626.5±55.0 °C(Predicted)
• PKA: 14.38±0.70(Predicted)
• Density: 1.282±0.06 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 5-Chloropentanamide Apixaban is an impurity of Apixaban (503612-47-3 #CAS), which is 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.

Technology Process of 5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide

There total 11 articles about 5-chloro-N-(4-(5-morpholino-6-oxo-3,6-dihydropyridin-1(2H)-yl)phenyl)pentanamide 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: 96.08%

5-Chlorovaleroyl chloride (1575-61-7) + 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one (1267610-26-3) → 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide (1643330-62-4)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 0 - 5 ℃; for 1h; Reagent/catalyst;

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide (1643330-62-4)

Guidance literature:

Multi-step reaction with 6 steps

1: triethylamine / tetrahydrofuran / 5 h / 5 - 20 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 2.5 h / 5 - 20 °C / Inert atmosphere

3: phosphorus pentachloride / chloroform / Reflux

4: 1 h / Reflux

5: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C

6: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere

With sodiumsulfide nonahydrate; phosphorus pentachloride; potassium tert-butylate; water; triethylamine; In tetrahydrofuran; ethanol; chloroform;

DOI:10.1080/00397911.2011.591956

Reference yield:

3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (503615-03-0) → 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide (1643330-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: water; sodiumsulfide nonahydrate / ethanol / 4 h / 50 °C

2: triethylamine / tetrahydrofuran / 2 h / 5 - 50 °C / Inert atmosphere

With sodiumsulfide nonahydrate; water; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1080/00397911.2011.591956

upstream raw materials:

5-Chlorovaleroyl chloride

1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one

4-nitro-aniline

5-chloro-N-(4-nitrophenyl)pentanamide

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF APIXABAN AND INTERMEDIATES THEREOF". Paragraph 0144. . Retrieved 2017/06/12.
• 2、 Jiang, Jian'An,Ji, Yafei. "Alternate synthesis of apixaban (BMS-562247), an inhibitor of blood coagulation factor Xa". . p. 72 - 79. Retrieved 2012/10/30.