反応 #7183

反応方程式

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

収率 75.9%

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

収率 75.9%

溶媒

DMF

反応条件

後処理

1. 1
   温度The reaction was then cooled
2. 2
   濃縮concentrated under reduced pressure
3. 3
   workup.ADDITIONdiluted with CH2Cl2 (35 mL) and saturated aqueous NaHCO3 (40 mL)
4. 4
   その他The phases were separated
5. 5
   洗浄the aqueous phase was washed with CH2Cl2 (2×25 mL)
6. 6
   洗浄The combined organic extracts were washed with saturated aqueous NaHCO3 (1×40 mL)
7. 7
   乾燥dried (NaSO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他Purification of the resultant oil by flash chromatography on silica gel (96:4 CH2Cl2/MeOH)

実験手順

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.

出典