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

HRID 1596253ノート

反応式

HRID 1596253 の反応式
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

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-764f10638f064788ae896b818ff45afb
出典データセット
uspto-grants-2001_09
特許番号
US06291455B1

反応ノート

読み込み中…