Reacción #164288

Ecuación de reacción

(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride

HATU

4-(N,N-dimethylamino)piperidine

→

NH3

title compound

Rendimiento 74.8%

(4-Dimethylamino-piperidin-1-yl)-{(R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidin-3-yl}-methanone

Rendimiento 74.8%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturacooled to room temperature
3. 3
   Lavadowashed with ammonium chloride solution (3 mL)
4. 4
   Filtraciónfiltered through a phase separator and organic solvent
5. 5
   Otrowas removed
6. 6
   OtroThe crude was then purified by SCX column (eluent

Procedimiento

Method N—Step a To a mixture of (R)-1-[3-(1-methyl-1H-benzoimidazol-2-yl)-phenyl]-piperidine-3-carboxylic acid hydrochloride (obtained as described in general method 1, step d) (0.01 g, 0.30 mmol) (obtained as described in method A, step d) in dcm (2.5 mL), HATU (0.12 g, 0.33 mmol), TEA (0.09 mL, 0.63 mmol) and 4-(N,N-dimethylamino)piperidine (0.04 g, 0.35 mmol) were added. The reaction mixture was heated at 35° C. overnight, cooled to room temperature, washed with ammonium chloride solution (3 mL), filtered through a phase separator and organic solvent was removed. The crude was then purified by SCX column (eluent: first dcm:MeOH/1:1 then NH3 in MeOH (2N)) and flash chromatography (eluent: gradient from EtOAc:NH3 in MeOH (2N)/10:0 to 9:1) to obtain 0.05 g of the title compound (37%).

Fuente