Ethanol → Deferasirox

HRID 1475615Notes

Reaction equation

HRID 1475615 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12](=O)[N:13]=1.[NH:19]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[NH2:20].C(O)C.S([O-])(O)(=O)=O.[K+]>O>[CH:16]1[CH:17]=[CH:18][C:10]([OH:9])=[C:11]([C:12]2[N:13]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[OH:1])[N:19]([C:21]3[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=3)[N:20]=2)[CH:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 120894-Hydrazinobenzoic acidHCID 516920Potassium bisulfateHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 214348Deferasirox

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
72.5 °C

Procedure

2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one (1.0 kg) and 4-Hydrazino benzoic acid (0.699 kg), Ethanol (9.0 lit), Water (1.0 lit) was stirred at 25-35° C. in round bottom flask. Followed by addition of Potassium hydrogen sulphate (0.15 kg) into the reaction mass and heated the reaction mass at 70-75° C. for two hrs. Cooled the reaction mass at 25-30° C. and stirred for 45 minutes. Filtered off the solid and washed with ethanol. Obtained solid and water (1.0 lit) stirred at 25-30° C. for 15 minutes and then heated at 50-55° C. for 1 hr. The solid was filtered at 50-55° C. and washed with water. Charge this wet cake in DMF (5.0 lit) and stirred at 25-30° C. In this solution 30% H2O2 was added at 25-30° C. within 1 hr. Followed by addition of water at 25-30° C. and stirred for 30 minutes. Filtered off the solid and washed it with water. The obtained solid was added in pre heated water and stirred at 45-50° C. Gradually increased the temperature up to 65-75° C. & stir it for 60 min. cooled the reaction mass at 45-50° C. and stirred it for 40 minutes. The precipitated Deferasirox filtered off and washed with water. Dry the solid at 65-75° C. in vacuum tray drier.

Workup

  1. temperatureCooled the reaction mass at 25-30° C.
  2. filtrationFiltered off the solid
  3. washwashed with ethanol
  4. customObtained solid and water (1.0 lit)
  5. stirringstirred at 25-30° C. for 15 minutes
  6. temperatureheated at 50-55° C. for 1 hr
  7. filtrationThe solid was filtered at 50-55° C.
  8. washwashed with water
  9. additionCharge this wet cake in DMF (5.0 lit)
  10. stirringstirred at 25-30° C
  11. additionIn this solution 30% H2O2 was added at 25-30° C. within 1 hr
  12. additionFollowed by addition of water at 25-30° C.
  13. stirringstirred for 30 minutes
  14. filtrationFiltered off the solid
  15. washwashed it with water
  16. additionThe obtained solid was added in pre
  17. temperatureheated water
  18. stirringstirred at 45-50° C
  19. temperatureGradually increased the temperature up to 65-75° C.
  20. stirringstir it for 60 min.
  21. temperaturecooled the reaction mass at 45-50° C.
  22. stirringstirred it for 40 minutes
  23. filtrationThe precipitated Deferasirox filtered off
  24. washwashed with water
  25. customDry the solid at 65-75° C. in vacuum tray drier

Sources & evidence

ORD record
ord-963d670f62324701910e8125586d9aba
Source dataset
uspto-grants-2015_04
Patent number
US09018389B2

Reaction notes

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