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

HRID 1364029ノート

反応式

HRID 1364029 の反応式
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

参加物

4

反応物 2

HCID 23665647Potassium tert-butoxideHCID 66958505HCID 66958505、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-92518614a1b7468390f4471b6eb0dd21
出典データセット
uspto-grants-2011_02
特許番号
US07888349B2

反応ノート

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