Potassium Carbonate → Ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoro-pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 610166ノート

反応式

HRID 610166 の反応式
C(O[CH:4]=[C:5]([C:11](=[O:22])[C:12]1[CH:17]=[C:16]([F:18])[C:15]([F:19])=[C:14]([Br:20])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.BrC1C(F)=C(C=C(F)C=1F)C(CC(OCC)=O)=O.[NH2:41][C:42]1[C:47]([F:48])=[CH:46][C:45]([F:49])=[C:44]([NH:50][C:51]([CH3:54])([CH3:53])[CH3:52])[N:43]=1.NC(=C)C([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl>[Br:20][C:14]1[C:15]([F:19])=[C:16]([F:18])[CH:17]=[C:12]2[C:13]=1[N:41]([C:42]1[C:47]([F:48])=[CH:46][C:45]([F:49])=[C:44]([NH:50][C:51]([CH3:54])([CH3:53])[CH3:52])[N:43]=1)[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]2=[O:22]

参加物

8

反応物 5

HCID 11430Potassium CarbonateHCID 10592111Ethyl 3-bromo-2,4,5-trifluorobenzoylacetateHCID 15896287N2-(tert-butyl)-3,5-difluoropyridine-2,6-diamineHCID 220225792-AminoacrylateHCID 54232143Ethyl 2-(3-bromo-2,4,5-trifluorobenzoyl)-3-ethoxyacrylate

生成物 1

HCID 15434899Ethyl 8-bromo-1-[6-(t-butylamino)-3,5-difluoro-pyridin-2-yl]-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To 5 ml of chloroform solution of ethyl 3-ethoxy-2-(3-bromo-2,4,5-trifluorobenzoyl)acrylate prepared from 1.32 g of ethyl 3-bromo-2,4,5-trifluorobenzoylacetate by normal process was added 2-amino-6-(t-butylamino)-3,5-difluoropyridine until completion of the conversion into the aminoacrylate form was confirmed by monitoring the reaction by TLC. The solution was concentrated under reduced pressure to obtain yellow solid residue. To this residue were added 1.2 g of anhydrous potassium carbonate and 2 ml of N,N-dimethylformamide, and the mixture was stirred at 90° C. for 15 minutes and allowed to cool. The solution was separated by adding 30 ml of chloroform and 300 ml of distilled water, and the chloroform layer was washed twice with 300 ml of distilled water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and allowed to stand. The precipitate was collected by filtration, washed with ethanol and diisopropylether successively to obtain 1.41 g of the title compound as a colorless powder.

後処理

  1. customthe reaction by TLC
  2. concentrationThe solution was concentrated under reduced pressure
  3. customto obtain yellow solid residue
  4. temperatureto cool
  5. customThe solution was separated
  6. additionby adding 30 ml of chloroform and 300 ml of distilled water
  7. washthe chloroform layer was washed twice with 300 ml of distilled water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. filtrationThe precipitate was collected by filtration
  11. washwashed with ethanol and diisopropylether successively

出典と根拠

ORDレコード
ord-f1bee19586e34ee9b3ca3e680cb1b46e
出典データセット
uspto-grants-1999_12
特許番号
US05998436

反応ノート

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