4-Hydrazinobenzoic acid → Deferasirox

HRID 1092194Notes

Reaction equation

HRID 1092194 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]>CN1CCCC1=O.C(O)(=O)CC>[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 90.8%

Reagents, catalysts & solvents 2

HCID 1032Propionic AcidSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °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 N-methylpyrrolidone and 5 ml of propionic acid is heated to 120° C. The mixture is maintained at this temperature and stirred for 1 hour. After completion of the reaction, the mixture is cooled and poured onto crushed ice. The resulting crystals are aspirated and washed with water. After drying, 0.99 g of raw deferasirox is obtained, i.e. 91% of the theory, with an HPLC content of 92.9% and a melting temperature of 250 to 261° C.

Workup

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

Sources & evidence

ORD record
ord-2ce8ea411d0b45bda4ee5489ff0c3401
Source dataset
uspto-grants-2012_03
Patent number
US08129421B2

Reaction notes

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