1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone

Base Information

• Chemical Name: 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone
• CAS No.: 1267610-26-3
• Molecular Formula: C15H19N3O2
• Molecular Weight: 273.335
• Mol file: 1267610-26-3.mol

Synonyms:1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone;1-(4-aMinophenyl)-3-Morpholino-5,6-dihydropyridin-2(1H)-one;2(1H)-Pyridinone, 1-(4-aMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-;Apixaba inretMediate A

Chemical Property of 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone

Chemical Property:

• Boiling Point: 491.5±45.0 °C(Predicted)
• PKA: 4.96±0.10(Predicted)
• PSA: 58.80000
• Density: 1.277±0.06 g/cm3(Predicted)
• LogP: 1.80570
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

99%min ^*data from raw suppliers

1-?(4-?Aminophenyl)?-?5,?6-?dihydro-?3-?(4-?morpholinyl)?-?2(1H)?-?pyridinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-?(4-?Aminophenyl)?-?5,?6-?dihydro-?3-?(4-?morpholinyl)?-?2(1H)?-?pyridinone 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.

Technology Process of 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone

There total 10 articles about 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone 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: 98.0%

3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one (503615-03-0) → 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one (1267610-26-3)

Guidance literature:

With hydrazine hydrate; In methanol; water; at 40 - 70 ℃; for 3h; Solvent; Temperature; Large scale;

Reference yield:

1-(4-nitrophenyl)piperidine-2-one (38560-30-4) → 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one (1267610-26-3)

Guidance literature:

Multi-step reaction with 3 steps

1: phosphorus pentachloride / chloroform / Reflux

2: 1 h / Reflux

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

With sodiumsulfide nonahydrate; phosphorus pentachloride; water; In ethanol; chloroform;

DOI:10.1080/00397911.2011.591956

Reference yield:

5-Chlorovaleroyl chloride (1575-61-7) → 1-(4-aminophenyl)-3-(morpholin-4-yl)-5,6-dihydropyridin-2(1H)-one (1267610-26-3)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1080/00397911.2011.591956

upstream raw materials:

4-nitro-aniline

5-Chlorovaleroyl chloride

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

1-(4-nitrophenyl)piperidine-2-one

Downstream raw materials:

5,6?dihydro?3?(4?morpholinyl)?1?[4?(2?oxo?1?piperidinyl)phenyl]?2(1H)?pyridone

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

5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide

Refernces

• 1、 -. "Preparation method of Apixaban intermediate". Paragraph 0042-0051. . Retrieved 2018/09/28.
• 2、 -. "PROCESS FOR THE PREPARATION OF APIXABAN AND INTERMEDIATES THEREOF". . . Retrieved 2017/06/12.