Tetrahydrofuran → HCID 178455216、化合物

HRID 388615ノート

反応式

HRID 388615 の反応式
[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]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 86633735HCID 86633735、化合物

生成物 1

HCID 178455216HCID 178455216、化合物収率 52.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1e035d8b6e774ea1926dd07963d1f8d3
出典データセット
uspto-grants-2013_02
特許番号
US08377957B2

反応ノート

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