Reacción #44285

Ecuación de reacción

6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline

pyrrolidin-3-ol

triethylamine

→

1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol

Rendimiento 99.5%

Disolventes

2-propanol

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction mixtures
2. 2
   Concentraciónconcentrated
3. 3
   OtroThe crude product was purified by flash chromatography
4. 4
   Otroa Horizon purification system in three batches (2×40M and 1×40S columns)
5. 5
   Lavadoeluting with chloroform/methanol (0.1-8%)
6. 6
   workup.DISSOLUTIONThe resulting solid was dissolved in chloroform containing 0.1% methanol (810 mL)
7. 7
   Lavadowashed with water and 1:1 water
8. 8
   Secadobrine, dried (MgSO4)
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated

Procedimiento

A mixture of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)quinoline (5.00 g, 14.7 mmol), pyrrolidin-3-ol (2.55 g, 29.3 mmol), and triethylamine (4.09 mL, 29.3 mmol) in 2-propanol (32 mL) was heated in the microwave for 30 minutes at 70° C. in two vials. The reaction mixtures were combined and concentrated. The crude product was purified by flash chromatography using a Horizon purification system in three batches (2×40M and 1×40S columns) eluting with chloroform/methanol (0.1-8%). The resulting solid was dissolved in chloroform containing 0.1% methanol (810 mL) and washed with water and 1:1 water:brine, dried (MgSO4), filtered and concentrated to afford 1-[1-(quinolin-6-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl]pyrrolidin-3-ol (5.08 g, 99%).

Fuente