Deferiprone → HCID 19862590, compound

HRID 1165165Notes

Reaction equation

HRID 1165165 reaction equation
C(N(CC)CC)C.[N:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]=[O:10].[OH:17][C:18]1[C:23](=[O:24])[CH:22]=[CH:21][N:20]([CH3:25])[C:19]=1[CH3:26]>C(#N)C.C(Cl)Cl>[CH2:15]([O:14][C:12]([CH2:11][NH:8][C:9]([O:17][C:18]1[C:23](=[O:24])[CH:22]=[CH:21][N:20]([CH3:25])[C:19]=1[CH3:26])=[O:10])=[O:13])[CH3:16]

Participants

6

Reactant 3

HCID 2972DeferiproneHCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetate2×

Product 1

HCID 19862590HCID 19862590, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

With stirring, 1.4 ml of triethylamine 1.7 ml of ethyl isocyanatoacetate are added at room temperature to a suspension of 1.39 g of 3-hydroxy-1,2-dimethyl-4(1H)-pyridinone in 100 ml of acetonitrile and 100 ml of methylene chloride, followed by the addition of 1.7 ml of ethyl isocyanatoacetate. The ensuing reaction is slightly exothermic. The solution that forms after about 15 minutes is concentrated by evaporation under reduced pressure after a further 45 minutes. The residue is dried under a high vacuum and crystallized from a mixture of methylene chloride and ethyl acetate. The crude crystalline product is taken up in 10 ml of methanol, insoluble material is removed by filtration, and the filtrate is concentrated by evaporation under reduced pressure. The residue is crystallised from a mixture of methylene chloride/ethyl acetate, affording 3-(ethoxycarbonylmethylaminocarbonyloxy)-1,2-dimethyl-4(1H)-pyridinone with a melting point of 132°-135° C.

Workup

  1. customThe ensuing reaction
  2. concentrationis concentrated by evaporation under reduced pressure after a further 45 minutes
  3. customThe residue is dried under a high vacuum
  4. customcrystallized from a mixture of methylene chloride and ethyl acetate
  5. custominsoluble material is removed by filtration
  6. concentrationthe filtrate is concentrated by evaporation under reduced pressure
  7. customThe residue is crystallised from a mixture of methylene chloride/ethyl acetate

Sources & evidence

ORD record
ord-25cfbeca498448caa7747c1ff13740b1
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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