Reaktion #629670

Reaktionsgleichung

Ethyl chloroformate

3-(imidazol-4-yl)propionic acid

triethylamine

DMF

4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine

DMF

→

N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at room temperature for 16 hours
3. 3
   SonstigeThe mixture was evaporated
4. 4
   Sonstigethe residue partitioned between EtOAc and 2N aqueous HCl
5. 5
   Extraktionextracted with EtOAc
6. 6
   Trocknendried (MgSO4)
7. 7
   Sonstigeevaporated to dryness
8. 8
   workup.DISSOLUTIONThe residual gum was dissolved in EtOAc
9. 9
   workup.ADDITIONtreated with excess of a solution of maleic acid in EtOAc
10. 10
    FiltrationThe resulting solid was filtered
11. 11
    Sonstigerecrystallised from EtOH/EtOAc

Vorschrift

Ethyl chloroformate (0.14 ml.) was added to a stirred mixture of 3-(imidazol-4-yl)propionic acid (0.3 g.) and triethylamine (2 ml.) in DMF (5 ml.) at 0° and the mixture stirred at 0° for 0.5 hours. 4-[2-(2,2,2-Trifluoroethyl)guanidino]-2-(5-aminopentyl)pyrimidine (0.3 g.) in DMF (2 ml.) was added to the mixture and stirring was continued at room temperature for 16 hours. The mixture was evaporated and the residue partitioned between EtOAc and 2N aqueous HCl. The acid layer was basified with 11N aqueous NaOH, extracted with EtOAc, dried (MgSO4) and evaporated to dryness. The residual gum was dissolved in EtOAc and treated with excess of a solution of maleic acid in EtOAc. The resulting solid was filtered and recrystallised from EtOH/EtOAc to give N-[5-(4-[2-(2,2,2-trifluoroethyl)guanidino]pyrimid-2-yl)pentyl]-3-(imidazol-4-yl)propionamide bis maleate hemihydrate (containing 0.5 EtOH of crystallisation) (0.2 g.), m.p. 136°-141° (decomp.).

Quelle