Potassium tert-butoxide → tert-butyl 10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate

HRID 1364029노트

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HRID 1364029 반응식
Cl[CH2:2][C:3]1[N:4]([CH2:16][CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[C:5]1[N:4]3[CH2:16][CH2:17][N:18]([C:19]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:25])[CH2:2][C:3]3=[N:15][C:6]=1[CH:7]=[N:8]2

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 66958505HCID 66958505, 화합물

생성물 1

HCID 66958138tert-butyl 10,11-dihydropyrazino[1',2':1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate수율 59.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Under a nitrogen atmosphere, a solution of tert-butyl 2-[2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (54.94 g, 152.3 mmol) in THF (400 mL) was cooled to 0° C.; a solution of potassium tert-butoxide (18.79 g of a 1 M solution in THF, 167.5 mmol) was added slowly. The reaction was stirred at 0° C. for three hours and then at ambient temperature overnight. The THF was removed under reduced pressure, and a 1:1 mixture of water and saturated aqueous sodium bicarbonate was added. The aqueous mixture was extracted with dichloromethane, and the combined extracts were washed sequentially with water and brine and concentrated under reduced pressure to provide 29.54 g of tert-butyl 10,11-dihydropyrazino[1′,2′:1,2]imidazo[4,5-c]quinoline-9(8H)-carboxylate.

후처리

  1. customat ambient temperature
  2. customovernight
  3. customThe THF was removed under reduced pressure
  4. additiona 1:1 mixture of water and saturated aqueous sodium bicarbonate
  5. additionwas added
  6. extractionThe aqueous mixture was extracted with dichloromethane
  7. washthe combined extracts were washed sequentially with water and brine
  8. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-92518614a1b7468390f4471b6eb0dd21
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888349B2

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