Dimethylformamide → 4-(4-Chloro-2-fluoroanilino)-7-(3-hydroxypropoxy)-6-methoxyquinazoline

HRID 1596253노트

반응식

HRID 1596253 반응식
Cl.C([O:9][CH2:10][CH2:11][CH2:12][O:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[F:32])=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:33][CH3:34])C1C=CC=CC=1.CN(C=O)C>[Pd].CO.ClC(Cl)Cl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([NH:24][C:18]2[C:17]3[C:22](=[CH:23][C:14]([O:13][CH2:12][CH2:11][CH2:10][OH:9])=[C:15]([O:33][CH3:34])[CH:16]=3)[N:21]=[CH:20][N:19]=2)=[C:26]([F:32])[CH:27]=1

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 226248927-(3-Benzyloxypropoxy)4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline hydrochloride

생성물 1

HCID 217015564-(4-Chloro-2-fluoroanilino)-7-(3-hydroxypropoxy)-6-methoxyquinazoline수율 33%

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

A mixture of 7-(3-benzyloxypropoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (180 mg, 0.4 mmol) and 5% palladium-on-charcoal catalyst (50 mg) in methanol (5 m), trichloromethane (5 ml) a nd DMF (1 ml) was stirred under hydrogen at 1 atmosphere pressure for 2 hours. The catalyst was removed by filtration through diatomaceous earth and the solvent removed by evaporation. The residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution, the organic layer separated and dried (MgSO4) and the solvent removed by evaporation. The residue was recrystallised from ethyl acetate/hexane to give 4-(4-chloro-2-fluoroanilino)-7-(3-hydroxypropoxy)-6-methoxyquinazoline (48 mg, 33%).

후처리

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed by evaporation
  3. customThe residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was recrystallised from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-764f10638f064788ae896b818ff45afb
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291455B1

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