4-Hydrazinobenzoic acid → Deferasirox

HRID 1092192Notes

Reaction equation

HRID 1092192 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)(=O)C(C)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

4

Reactant 2

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

Product 1

HCID 214348DeferasiroxYield 48.6%

Reagents, catalysts & solvents 1

HCID 612Lactic AcidSolvent

Conditions

Temperature
115 °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 lactic acid is heated to its boiling point and maintained at this temperature (115° C.) for 2 hours. After completion of the reaction the mixture is cooled down, causing separation of the crystalline product. 5 ml of ethyl acetate are added. After drying, 0.53 g of raw deferasirox is obtained, i.e. 49% of the theory, with an HPLC content of 94% and a melting temperature of 248 to 260° C.

Workup

  1. temperatureis heated to its boiling point
  2. customAfter completion of the reaction the mixture
  3. temperatureis cooled down
  4. customseparation of the crystalline product
  5. addition5 ml of ethyl acetate are added
  6. customAfter drying

Sources & evidence

ORD record
ord-443e30c22d7a4dd6aa92e7786bc255c1
Source dataset
uspto-grants-2012_03
Patent number
US08129421B2

Reaction notes

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