Acetic Acid → Rivaroxaban

HRID 1054150Notes

Reaction equation

HRID 1054150 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([N:9](C=O)[CH2:10][C@@H:11]2[O:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][C:24]4=[O:29])=[CH:19][CH:18]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1.C(O)(=O)C.Cl>CO>[CH:19]1[C:20]([N:23]2[C:24](=[O:29])[CH2:25][O:26][CH2:27][CH2:28]2)=[CH:21][CH:22]=[C:17]([N:13]2[C:14](=[O:16])[O:15][C@@H:11]([CH2:10][NH:9][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:8])[CH2:12]2)[CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 76072855HCID 76072855, compound

Product 1

HCID 9875401Rivaroxaban

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

5-chloro-N-formyl-N-({(5 S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)thiophene-2-carboxamide (1.0 g) taken in mixture of acetic acid (5 ml) and conc hydrochloric acid (0.25 ml). Obtained reaction mixture is heated to 70 to 80° C. for 3 to 4 h. After completion of reaction, cooled reaction mixture 25 to 30° C. and added methanol (5 ml). The precipitated solid is filtered off and washed by methanol (3 ml).

Workup

  1. customObtained
  2. customreaction mixture
  3. customAfter completion of reaction
  4. temperaturecooled
  5. customreaction mixture 25 to 30° C.
  6. filtrationThe precipitated solid is filtered off
  7. washwashed by methanol (3 ml)

Sources & evidence

ORD record
ord-65f31bd2226b49e0bea67cafd205a6e9
Source dataset
uspto-grants-2016_07
Patent number
US09394292B2

Reaction notes

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