1,1'-Carbonyldiimidazole → HCID 58948148, compound

Temperature

60 °C

CDI (184 mg, 1.13 mmol) was added to a solution of the N*2*,N*4*-Dibenzyl-6-(1-methyl-1H-imidazol-2-yl)-pyridine-2,3,4-triamine (218 mg, 0.567 mmol) in DMF (3 ml) in a ReactiVial. The vial was flushed with nitrogen then sealed and heated in an aluminium block at 60° C. (block temperature). The dark brown solution was left to stir at this temperature for 16 hrs. The solution was concentrated under high-vacuum then dissolved in concentrated sulphuric acid (5 ml). The brown solution was left to stir at room temperature for 30 minutes then poured onto crushed ice (˜20 ml). A saturated aqueous solution of potassium carbonate was added drop-wise until pH˜8. The aqueous solution was decanted from the solid that had precipitated out during neutralisation, then extracted with EtOAc (2×50 ml). The combined organics were dried (MgSO4) and evaporated to a yellow solid (106 mg).

1. customThe vial was flushed with nitrogen
2. customthen sealed
3. waitThe dark brown solution was left
4. concentrationThe solution was concentrated under high-vacuum
5. dissolutionthen dissolved in concentrated sulphuric acid (5 ml)
6. waitThe brown solution was left
7. stirringto stir at room temperature for 30 minutes
8. additionthen poured
9. customonto crushed ice (˜20 ml)
10. additionA saturated aqueous solution of potassium carbonate was added drop-wise until pH˜8
11. customThe aqueous solution was decanted from the solid
12. customthat had precipitated out during neutralisation
13. extractionextracted with EtOAc (2×50 ml)
14. dry with materialThe combined organics were dried (MgSO4)
15. customevaporated to a yellow solid (106 mg)

ORD record

ord-e762f052b36e48b9a7baa071b4ad01d2

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691877B2