4-Hydrazinobenzoic acid → Deferasirox

HRID 1092195Notes

Reaction equation

HRID 1092195 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]>ClC(Cl)(Cl)C(O)=O.C1(C)C=CC=CC=1>[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 2

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

Product 1

HCID 214348DeferasiroxYield 55%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6421Trichloroacetic AcidSolvent

Conditions

Temperature
110 °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 g of trichloroacetic acid and 5 ml of toluene is heated to 110° C. The mixture is maintained and stirred at this temperature for 3 hours. After completion of the reaction, the mixture is cooled and poured onto crushed ice. The resulting crystals are aspirated and washed with water and ethyl acetate. After drying, 0.6 g of raw deferasirox is obtained, i.e. 55% of the theory, with an HPLC content of 99.56% and a melting temperature of 258 to 262° C.

Workup

  1. temperatureThe mixture is maintained
  2. customAfter completion of the reaction
  3. temperaturethe mixture is cooled
  4. additionpoured
  5. customonto crushed ice
  6. washwashed with water and ethyl acetate
  7. customAfter drying

Sources & evidence

ORD record
ord-37518feb4b82461f84686015f36dc57a
Source dataset
uspto-grants-2012_03
Patent number
US08129421B2

Reaction notes

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