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

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1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone 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
  • Apixaban Impurity 47
  • Apixaban intA
  • Apixaban related impurities 2
CAS:
1267610-26-3
MF:
C15H19N3O2
MW:
273.33
EINECS:
125-745-3
Mol File:
1267610-26-3.mol
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1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone Chemical Properties

Melting point:
>246°C (dec.)
Boiling point:
491.5±45.0 °C(Predicted)
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)
form 
Solid
pka
4.96±0.10(Predicted)
color 
Off-White to Pale Beige
InChI
InChI=1S/C15H19N3O2/c16-12-3-5-13(6-4-12)18-7-1-2-14(15(18)19)17-8-10-20-11-9-17/h2-6H,1,7-11,16H2
InChIKey
YUGIGSPFTMLIMA-UHFFFAOYSA-N
SMILES
C1(=O)N(C2=CC=C(N)C=C2)CCC=C1N1CCOCC1
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1-(4-AMinophenyl)-5,6-dihydro-3-(4-Morpholinyl)-2(1h)-pyridinone Usage And Synthesis

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


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%.

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.

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