Ethyl Acetate → Deferasirox

HRID 1092196Notes

Reaction equation

HRID 1092196 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(OCC)(=O)C>COC(C)C(O)=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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 120894-Hydrazinobenzoic acidHCID 1356857232-(2-Hydroxyphenyl)-4H-1,3-benzoxazin-4-one

Product 1

HCID 214348DeferasiroxYield 60.5%

Reagents, catalysts & solvents 1

HCID 922092-Methoxypropanoic acidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 0.7 g (2.92 mmol) of 2-(2-hydroxyphenyl)benz[e][1,3]oxazin-4-one and 0.52 g (3.44 mmol) of 4-hydrazinobenzoic acid in 5 ml of methoxypropionic acid is heated to 100° C. The mixture is maintained and stirred at this temperature for 1 hour. After completion of the reaction, the mixture is cooled and 5 ml of ethyl acetate are added. The resulting mixture is stirred for 10 minutes, then it is filtered and the crystals are washed with ethyl acetate. After drying, 0.66 g of raw deferasirox is obtained, i.e. 60% of the theory, with an HPLC content of 99.3% and a melting temperature of 259 to 263° C.

Workup

  1. temperatureThe mixture is maintained
  2. customAfter completion of the reaction
  3. temperaturethe mixture is cooled
  4. stirringThe resulting mixture is stirred for 10 minutes
  5. filtrationit is filtered
  6. washthe crystals are washed with ethyl acetate
  7. customAfter drying

Sources & evidence

ORD record
ord-41c1b194ec8f4efba877b9e793596bbb
Source dataset
uspto-grants-2012_03
Patent number
US08129421B2

Reaction notes

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