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

HRID 591800노트

반응식

HRID 591800 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fa6159f0496f4bfd8dbfc5c77de8cef5
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238640B2

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