Reacción #53440

Ecuación de reacción

6-bromopyrrolo[1,2-a]pyrazine-3-carboxylic acid hydrochloride

dihydrochloride

DIEA

HATU

→

N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide

Disolventes

DMF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónis concentrated to dryness under reduced pressure
2. 2
   OtroThe resulting material is absorbed to silica gel
3. 3
   Otropurified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent)
4. 4
   Otrocrystallized from EtOH/acetone/Et2O
5. 5
   Otroto give an off white spheres

Procedimiento

To a suspension of 6-bromopyrrolo[1,2-a]pyrazine-3-carboxylic acid hydrochloride (1.67 mmol), (R)-3-aminoquinulidine dihydrochloride (0.34 g, 1.67 mmol), DIEA (1.5 mL, 8.35 mmol) in DMF (20 mL) and THF (10 mL) is added HATU (0.64 g, 1.67 mmol). The resulting suspension is stirred for 16 h at which time it is concentrated to dryness under reduced pressure. The resulting material is absorbed to silica gel and purified with silica gel chromatography (9% MeOH/1%NH3OH/CH2Cl2 as the eluent) salted with fumeric acid, and crystallized from EtOH/acetone/Et2O to give an off white spheres. Yield 45%. HRMS (FAB) calcd. for C15H17BrN4O+H 349.0664, found 349.0647.

Fuente