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

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

Used in Pharmaceutical Industry:
1-(4-Aminophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1H)-pyridinone is used as a key intermediate in the synthesis of Apixaban (A726700) for its potential as a new oral coagulant. 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone contributes to the development of medications that may be useful in the prevention of venous thromboembolism in total hip and knee replacement orthopedic surgeries, as well as in the treatment of patients with venous thromboembolic disorders or atrial fibrillation.
Used in Research and Development:
1-(4-Aminophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1H)-pyridinone is utilized in research and development for the exploration of new therapeutic agents targeting coagulation factor Xa. 1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone aids in the advancement of innovative treatments for various thrombotic conditions, enhancing patient care and outcomes.

Synthesis

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.

Synthesis

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

• 4789-09-7 1-phenylpiperidin-2-one 
• 62-53-3 aniline 
• 91131-23-6 5-chloro-pentanoic acid phenylamide 
• 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 
• 2187409-01-2 6-(4-((5-amino-5-oxopentyl)amino)phenyl)-1-(4-methoxyphenyl)‐7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxamide 

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 method of Apixaban intermediate

The invention relates to synthesis of an Apixaban intermediate, in particular to synthesis of 4-cyclic lactam aniline compounds. The synthesis is implemented with a method shown as the formula in thedescription, the synthetic route is novel, the operation

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.

PROCESS FOR THE PREPARATION OF APIXABAN AND INTERMEDIATES THEREOF

The present invention refers to novel process for the preparation of Apixaban. Further, the invention also related to a process for the preparation of intermediate of Apixaban from very basic and cheap row material i.e. Aniline which is widely commercially available. The present invention provides process for preparation of Apixaban using a different sequence of synthetic steps and does not involve use of Ullmann reaction.

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.

A method of preparing intermediates [...]

A disclosed preparation method for an apixaban intermediate comprises the following steps: step (1), performing an amidation reaction shown in the specification on a compound 3 and a compound M in an organic solvent under the effect of an organic alkali to obtain a reaction solution containing a compound 3'; and step (2), under the effect of an inorganic base, directly performing an nucleophilic substitution reaction shown in the specification on the reaction solution obtained in the step (1) to prepare a compound 4, and performing a nitration reaction on the compound 4 under the effect of concentrated sulfuric acid and concentrated nitric acid to prepare a compound 5. The preparation method provided by the invention is low in cost, simple in operation and suitable for industrialization.

A pyridine derivative

The present invention relates to the field of pharmaceutical chemistry, specifically to a class of compounds containing lactam and derivative thereof, and especially to a pyridine derivative as shown in general formula (I), preparation method and the use thereof as a Factor Xa inhibitor. The present invention further relates to the medical use of the compound and derivative thereof in preparation of anticoagulant drugs, particularly to the use in preparation of drugs for preventing or treating thrombosis or embolism.

4-process for the preparation of cyclic lactam base aniline

The invention relates to the field of medicines, specifically relates to a preparation method of an aniline compound and particularly relates to a preparation method of 4-cyclic lactam group aniline. A synthesis method of the 4-cyclic lactam group aniline

Alternate synthesis of apixaban (BMS-562247), an inhibitor of blood coagulation factor Xa

An alternate approach to apixaban was described. The synthesis features a novel and cost-effective synthetic strategy to construct a key N-phenylvalerolactam intermediate 4 from 4-nitroaniline. In addition, the modified synthetic route avoids the use of expensive reagents and significantly improves reaction yields. As demonstrated practically, apixaban was successfully synthesized in overall good yield (35%). Copyright Taylor & Francis Group, LLC.