Water → N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide

HRID 1862225ノート

反応式

HRID 1862225 の反応式
O.[F:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([O:12][C:13]2[C:14]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][C:4]=1[NH:25][C:26](=[O:28])[CH3:27]>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[NH2:9][C:7]1[C:6]([O:12][C:13]2[C:14]([O:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:5][C:4]([NH:25][C:26](=[O:28])[CH3:27])=[C:3]([F:2])[CH:8]=1

参加物

6

反応物 2

HCID 962WaterHCID 21933549N-[2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}-4-nitrophenyl]acetamide

生成物 1

HCID 21933527N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide収率 91.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
45 °C

実験手順

To a mixture of 3.6 g of an iron powder, 10 ml of acetic acid and 1 ml of water was added a solution of 3.67 g of N-[2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyloxy}-4-nitrophenyl]acetamide in 12 ml of acetic acid and 2 ml of ethyl acetate, dropwise while maintaining the temperature of the reaction solution at 45° C. or lower. After completion of the addition, the mixture was stirred for 1 hour at 40° C., then, the reaction mixture was filtrated through Celite, and concentrated. The residue was diluted with saturated aqueous sodium bicarbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated. Then, the resulted residue was washed with diisopropyl ether to obtain 3.09 g of N-[4-amino-2-fluoro-5-{2-(methoxycarbonyl)methoxy-3-pyridyl oxy}phenyl]acetamide.

後処理

  1. additionAfter completion of the addition
  2. filtrationthe reaction mixture was filtrated through Celite
  3. concentrationconcentrated
  4. additionThe residue was diluted with saturated aqueous sodium bicarbonate solution
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washThen, the resulted residue was washed with diisopropyl ether

出典と根拠

ORDレコード
ord-8a09c8dffc424929a10809ed4221c01f
出典データセット
uspto-grants-2003_03
特許番号
US06537948B1

反応ノート

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