Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate → Ethyl 8-chloro-1-(3,5-difluoro-6-methoxypyridin-2-yl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 368431ノート

反応式

HRID 368431 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]([Cl:20])[C:13]=1F)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.ClC1C(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]([O:50][CH3:51])[N:43]=1.NC(=C)C([O-])=O>C(Cl)(Cl)Cl>[Cl: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]([O:50][CH3:51])[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

6

反応物 4

HCID 10934859Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoateHCID 220225792-AminoacrylateHCID 221212643,5-Difluoro-6-methoxypyridin-2-amineHCID 54402571Ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate

生成物 1

HCID 22121219Ethyl 8-chloro-1-(3,5-difluoro-6-methoxypyridin-2-yl)-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
90 °C

実験手順

To 3 ml chloroform solution of ethyl 3-ethoxy-2-(3-chloro-2,4,5-trifluorobenzoyl)acrylate prepared from 0.78 g of ethyl 3-chloro-2,4,5-trifluorobenzoylacetate by normal process was added 2-amino-3,5-difluoro-6-methoxypyridine until completion of the conversion into the aminoacrylate form was confirmed by monitoring the reaction by TLC. The solution was concentrated under reduced pressure, and to the residue were added 0.80 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 to obtain 615 mg of the title compound as a pale brown powder.

後処理

  1. customthe reaction by TLC
  2. concentrationThe solution was concentrated under reduced pressure
  3. additionto the residue were added 0.80 g of anhydrous potassium carbonate and 2 ml of N,N-dimethylformamide
  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

出典と根拠

ORDレコード
ord-3b7ed81ea74842db9369c002e6b14f4d
出典データセット
uspto-grants-2000_10
特許番号
US06133284

反応ノート

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