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Dichloromethane → Rivaroxaban

HRID 1054153
Notes
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Reaction equation

HRID 1054153 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:20][NH:21][CH:22]=[O:23])[O:3]1.ClCCl.[N+](C1C=CC([C:36]2[CH:40]=[C:39]([Cl:41])[S:38][C:37]=2C([O-])=O)=CC=1)([O-])=O.[OH-].[Na+]>O.CO.C(O)(=O)C>[CH:11]1[C:10]([N:13]2[C:14](=[O:19])[CH2:15][O:16][CH2:17][CH2:18]2)=[CH:9][CH:8]=[C:7]([N:6]2[C:2](=[O:1])[O:3][C@@H:4]([CH2:20][NH:21][C:22]([C:37]3[S:38][C:39]([Cl:41])=[CH:40][CH:36]=3)=[O:23])[CH2:5]2)[CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 6344Dichloromethane2×HCID 14798Sodium HydroxideHCID 90258317Rivaroxaban Impurity 116HCID 902586624-Nitrophenyl-5-chlorothiophene-2-carboxylate

Product 1

HCID 9875401Rivaroxaban

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 887MethanolSolvent
HCID 962WaterSolvent

Procedure

N-({(5 S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide (1 g) taken in a dichloromethane(10 ml) and stirred reaction mass at 25 to 30° C. for 30 minutes. To this mixture added solution of 4-nitrophenyl-5-chlorothiophene-2-carboxylate (1.06 g) in a dichloromethane (10 ml) and sodium hydroxide (0.38 g) in water (5 ml) simultaneously through addition funnel. Obtained reaction mass then stirred for 1 to 2 h at 25 to 30° C. After completion of reaction, Separated organic layer and concentrated under reduced pressure to obtain residue. Added acetic acid and methanol to residue stirred for 30 minutes and obtained solid is filtered off. Washed solid with methanol.

Workup

  1. customreaction mass at 25 to 30° C. for 30 minutes
  2. additionsimultaneously through addition funnel
  3. customObtained
  4. customreaction mass
  5. stirringthen stirred for 1 to 2 h at 25 to 30° C
  6. customAfter completion of reaction
  7. customSeparated organic layer
  8. concentrationconcentrated under reduced pressure
  9. customto obtain residue
  10. customobtained solid
  11. filtrationis filtered off
  12. washWashed solid with methanol

Sources & evidence

ORD record
ord-ecaac78c675f493183d48d548706c34e
Source dataset
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09394292B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes