1267610-26-3

Basic information

• Product Name: 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone
• 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;Apixaban Impurity S
• CAS NO: 1267610-26-3
• Molecular Formula: C₁₅H₁₉N₃O₂
• Molecular Weight: 273.33026
• EINECS: -0
• Mol File: 1267610-26-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 491.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.277±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.96±0.10(Predicted)
• CAS DataBase Reference: 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone(1267610-26-3)
• EPA Substance Registry System: 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone(1267610-26-3)

Safety Data

• Hazardous Substances Data: 1267610-26-3(Hazardous Substances Data)

Usage

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.

Synthesis

Different sources of media describe the Synthesis of 1267610-26-3 differently. You can refer to the following data:
1. 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production In the process.
2. Add 25L of water and 25L of methanol to the 500L reactor, add 2.5kg of compound (I) and 250g of Raney cobalt under stirring, raise the temperature to 40-50 °C, slowly add 2.0kg of hydrazine hydrate (content 80%), keep warm 60-70 °C, reaction for 3h, the reaction was completed, filtered with diatomaceous earth, concentrated solvent was removed, and MTBE was added to the filter cake.2.20 kg of a white solid were obtained with a yield of 98% and a purity of 99.8%.

Upstream product

• 91131-23-6 5-chloro-pentanoic acid phenylamide 
• 62-53-3 aniline 
• 4789-09-7 1-phenylpiperidin-2-one 
• 881386-01-2 3,3-dichloro-1-(4-nitrophenyl)piperidine-2-one 
• 503615-03-0 3-(morpholin-4-yl)-1-(4-nitrophenyl)-5,6-dihydropyridin-2(1H)-one 
• 38560-30-4 1-(4-nitrophenyl)piperidine-2-one 
• 1039914-85-6 5-chloro-N-(4-nitrophenyl)pentanamide 
• 1575-61-7 5-Chlorovaleroyl chloride 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 545445-44-1 5,6?dihydro?3?(4?morpholinyl)?1?[4?(2?oxo?1?piperidinyl)phenyl]?2(1H)?pyridone 
• 503614-91-3 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 
• 1643330-62-4 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide 
• 2098457-93-1 5,6-dihydro-3-(4-morpholinyl)-1-[4-(2-oxo-6-methyl-1-piperidinyl)phenyl]-2(1H)-pyridone 
• 2098457-92-0 apixaban 

Relevant articles and documents

Preparation method of apixaban intermediate suitable for industrial production

The invention discloses a synthesis method of an apixaban intermediate suitable for industrial production. The method comprises the following steps: carrying out phase-transfer catalytic amidation reaction on paranitroaniline and 5-chlorovaleryl chloride in an organic phase and water phase two-phase system under an inorganic weakly alkaline condition to obtain an APM01 solution, and adding a sodium hydroxide water solution, and cyclizing in a pot to obtain an APM02 solution; directly carrying out alpha-reactive hydrogen dichlorination on an APM02 organic solution and phosphorus pentachloride after simple acid pickling, liquid separation and drying to obtain an APM03 solution; carrying out condensation-elimination reaction on the APM03 solution and excessive morpholine after simple acid pickling and liquid separation, and carrying out simple crystallization and purification treatment to separate out an APM04 solid, and reducing the APM04 into APM05 by sodium sulfide; and carrying out amidation-cyclization two-step one-pot reaction on the APM05 and 5-chlorovaleryl chloride to prepare a key intermediate APM07. According to the method, the synthesis efficiency of the apixaban intermediate is improved, the reaction is mild, and dangerous NaH and other expensive reagents are not used, so that the production cost is saved, the operation is simple, and the method is suitable for industrial popularization.

PREPARATION OF ACTIVE PHARMACEUTICAL INGREDIENTS AND INTERMEDIATES THEREOF

The present invention provides processes for the preparation of active pharmaceutical ingredients and intermediates thereof in an aqueous designer smart surfactant solution.

DIMER IMPURITIES OF APIXABAN AND METHOD TO REMOVE THEM

Object of the present invention are dimer impurities of the active ingredient Apixaban, analytical methods for identifying and/or quantifying them and a synthetic method for removing or limiting said impurities from Apixaban and synthetic precursors thereof.