تفاعل #629670

معادلة التفاعل

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

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued at room temperature for 16 hours
3. 3
   أخرىThe mixture was evaporated
4. 4
   أخرىthe residue partitioned between EtOAc and 2N aqueous HCl
5. 5
   استخلاصextracted with EtOAc
6. 6
   تجفيفdried (MgSO4)
7. 7
   أخرىevaporated 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
    ترشيحThe resulting solid was filtered
11. 11
    أخرىrecrystallised from EtOH/EtOAc

الإجراء التجريبي

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.).

المصدر