Hexane → 7-Acetoxy4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline

HRID 634677

반응식

HRID 634677 반응식
[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9](=O)[NH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2].S(Cl)(Cl)=O.[CH2:22]([O:29][C:30]1[C:31]([CH3:38])=[CH:32][C:33]([F:37])=[C:34]([CH:36]=1)[NH2:35])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCCCCC>CN(C=O)C.C(O)(C)C>[C:1]([O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([NH:35][C:34]3[CH:36]=[C:30]([O:29][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:31]([CH3:38])=[CH:32][C:33]=3[F:37])=[N:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:16][CH3:17])(=[O:3])[CH3:2]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 24386Thionyl ChlorideHCID 219910685-Benzyloxy-2-fluoro-4-methylanilineHCID 1356979057-Acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one

생성물 1

HCID 212603127-Acetoxy4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline수율 43%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 3776Isopropanol용매

실험 절차

A mixture of 7-acetoxy-6-methoxy-3,4-dihydroquinazolin-4-one (1.69 g, 7.2 mmol), thionyl chloride (50 ml) and DMF (3 drops) was heated at reflux for 2 hours. The excess thionyl chloride was removed by evaporation and the residue azeotroped with toluene. The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution. The organic phase was separated, dried (MgSO4) and the solvent removed by evaporation. 5-Benzyloxy-2-fluoro-4-methylaniline (1.8 g, 7.8 mmol) in isopropanol (50 ml) was added to the residue and the mixture heated at reflux for 2 hours. The mixture was allowed to cool, hexane added and the precipitated product collected by filtration to give 7-acetoxy-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (1.34 g, 43%).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 2 hours
  3. customThe excess thionyl chloride was removed by evaporation
  4. customthe residue azeotroped with toluene
  5. customThe residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate solution
  6. customThe organic phase was separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. temperaturethe mixture heated
  10. temperatureat reflux for 2 hours
  11. temperatureto cool
  12. filtrationthe precipitated product collected by filtration

출처 및 근거

ORD 기록
ord-ebb58f8a97c24a4e87a477c597871eff
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06184225B2

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