Reacción #7183

Ecuación de reacción

5-benzoyl-2-chloromethylbenzimidazole

N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

N,N-diisopropylethylamine

→

product

Rendimiento 75.9%

N-(2-pyridinylmethyl)-N′-(5-benzoyl-1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Rendimiento 75.9%

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was then cooled
2. 2
   Concentraciónconcentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL)
4. 4
   OtroThe phases were separated
5. 5
   Lavadothe aqueous phase was washed with CH2Cl2 (2×25 mL)
6. 6
   LavadoThe combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL)
7. 7
   Secadodried (NaSO4)
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated under reduced pressure
10. 10
    OtroPurification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH)

Procedimiento

A solution of 5-benzoyl-2-chloromethylbenzimidazole (284 mg, 1.05 mmol), N-(tert-butoxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (476 mg, 1.04 mmol) and N,N-diisopropylethylamine (0.36 mL, 2.08 mmol) were stirred at 80□ C in DMF (4 mL) for 16 hours. The reaction was then cooled, concentrated under reduced pressure and diluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL). The phases were separated and the aqueous phase was washed with CH2Cl2 (2×25 mL). The combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL), dried (NaSO4), filtered and concentrated under reduced pressure. Purification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH) provided the desired alkylated product (468 mg, 65%) as an orange oil.

Fuente