Hydrochloric Acid → 2-[7-(4-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamide

HRID 7627

반응식

HRID 7627 반응식
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[NH:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].FC1C=CC(CO)=CC=1.FC1C=C2[C:36]([C:37](=[O:43])[NH:38]C=N2)=CC=1.Cl>CN(C=O)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][O:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:18])[N:13]([CH2:36][C:37]([NH2:38])=[O:43])[CH:14]=[N:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 680224-Fluorobenzylic alcoholHCID 1353984967-Fluoroquinazolin-4(3H)-oneHCID 1357527157-(4-Fluoro-benzyloxy)-3H-quinazolin-4-one

생성물 1

HCID 100878132-[7-(4-Fluoro-benzyloxy)-4-oxo-4H-quinazolin-3-yl]-acetamide수율 66%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

7-(4-Fluoro-benzyloxy)-3H-quinazolin-4-one: A mixture of sodium hydride (55%, 3.2 g, 73 mmol), 4-fluorobenzyl alcohol (9.2 g, 73 mmol) and 7-fluoro-3H-quinazolin-4-one (3.0 g, 18 mmol) in DMF (75 mL) was heated at 140° C. for 2 h. The resulting suspension was cooled to rt and the mixture acidified to pH 3 with HCl (conc.). The resulting precipitate was then filtered off, washed with water and diethylether. Partial purification by chromatography on silica gel eluting with ethyl acetate:hexane (2:1) afforded the title compound (3.2 g, 66%) as an off-white solid. MS: m/e=271.3 (M+H+).

후처리

  1. temperatureThe resulting suspension was cooled to rt
  2. filtrationThe resulting precipitate was then filtered off
  3. washwashed with water and diethylether
  4. customPartial purification by chromatography on silica gel eluting with ethyl acetate:hexane (2:1)

출처 및 근거

ORD 기록
ord-02ebb08f2555436889139e7598c8df89
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087612B2

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