Water → 7-(2-(Benzyloxy)ethoxy)-5-methoxy-2-(pyridin-4-yl)quinazolin-4(3H)-one

HRID 591800ノート

反応式

HRID 591800 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].F[C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:31])[NH:20][C:21]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[N:22]2)=[C:17]([O:32][CH3:33])[CH:16]=1.O>CS(C)=O.C(O)(=O)C>[CH2:1]([O:8][CH2:9][CH2:10][O:11][C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:31])[NH:20][C:21]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[N:22]2)=[C:17]([O:32][CH3:33])[CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 121412-(Benzyloxy) ethanolHCID 24758Sodium hydrideHCID 1363480537-fluoro-5-methoxy-2-pyridin-4-yl-3H-quinazolin-4-one

生成物 1

HCID 1359390637-(2-(Benzyloxy)ethoxy)-5-methoxy-2-(pyridin-4-yl)quinazolin-4(3H)-one

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of 2-benzyloxy-ethanol (2 mL) in dimethyl sulfoxide (3 mL) was added sodium hydride (0.30 g, 7.4 mmol) in portions, and the reaction mixture was stirred at room temperature for 45 minutes. To this mixture was added 7-fluoro-5-methoxy-2-pyridin-4-yl-3H-quinazolin-4-one (0.20 g, 0.74 mmol) and the reaction mixture was heated at 80° C. for 16 hours. Water was added, the mixture was acidified with acetic acid to pH approximately 4-5, and the precipitated solid was filtered off, to obtain a crude product, which was purified by preparative HPLC to obtain the title compound as a light yellow solid. Yield: 0.12 g (40%). MP 228.2-229.9° C. 1H NMR (400 MHz, DMSO-d6): δ12.29 (s, 1H), 8.77 (d, 2H), 8.08 (d, 2H), 7.36 (m, 5H), 6.82 (s, 1H), 6.62 (s, 1H), 4.58 (s, 2H), 4.32 (t, 2H), 3.87 (s, 3H), 3.83 (t, 2H). MS (ES+) m/z: 404.51 (M+1).

後処理

  1. temperaturethe reaction mixture was heated at 80° C. for 16 hours
  2. filtrationthe precipitated solid was filtered off
  3. customto obtain a crude product, which
  4. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-fa6159f0496f4bfd8dbfc5c77de8cef5
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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