Tetrahydrofuran → HCID 178455216, 화합물

HRID 388615노트

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HRID 388615 반응식
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][NH:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:29]=[C:28]([Cl:36])[C:27]=1[NH2:37])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C1COCC1>N1C=CC=CC=1>[Si:13]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:26]2[C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:29]=[C:28]([Cl:36])[C:27]=2[N:37]=[C:1]1[OH:2])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86633735HCID 86633735, 화합물

생성물 1

HCID 178455216HCID 178455216, 화합물수율 52.1%

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
80 °C

실험 절차

1,1′-Carbonyldiimidazole (32.6 g, 201 mmol) was added to a solution of N4-[4-(tert-butyldimethylsilanyloxy)butyl]-2-chloroquinoline-3,4-diamine (50.96 g, 134.1 mmol), THF (250 mL), and pyridine (250 mL), and the reaction was heated at 80° C. overnight and allowed to cool. The volatiles were removed under reduced pressure. The residue was dissolved in ethyl acetate (600 mL), and the resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL) and then concentrated under reduced pressure. The resulting solid was triturated with diethyl ether (1 L), collected by filtration, washed with diethyl ether (800 mL), and dried under vacuum for 30 minutes to provide 28.39 g of 1-[4-(tert-butyldimethylsilanyloxy)butyl]-4-chloro-1H-imidazo[4,5-c]quinolin-2-ol as a white solid.

후처리

  1. temperatureto cool
  2. customThe volatiles were removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate (600 mL)
  4. washthe resulting solution was washed sequentially with brine (2×400 mL) and water (2×400 mL)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting solid was triturated with diethyl ether (1 L)
  7. filtrationcollected by filtration
  8. washwashed with diethyl ether (800 mL)
  9. customdried under vacuum for 30 minutes

출처 및 근거

ORD 기록
ord-1e035d8b6e774ea1926dd07963d1f8d3
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377957B2

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