Isopropanol → 3-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propan-1-ol

HRID 1926061ノート

反応式

HRID 1926061 の反応式
ClC1C=C(N[C:18]2[C:19]3[N:26]([CH2:27][C:28](O)=O)[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)C=CC=1OCC1C=CC=C(F)C=1.[Cl:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][C:38]=1[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=1)[NH2:35].[CH:50]([OH:53])(C)C>C(=O)([O-])O.[Na+]>[Cl:31][C:32]1[CH:33]=[C:34]([NH:35][C:18]2[C:19]3[N:26]([CH2:27][CH2:28][CH2:50][OH:53])[CH:25]=[CH:24][C:20]=3[N:21]=[CH:22][N:23]=2)[CH:36]=[CH:37][C:38]=1[O:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:47])([F:48])[F:49])[CH:41]=1

参加物

5

反応物 3

HCID 3776IsopropanolHCID 196269843-Chloro-4-[3-(trifluoromethyl)phenoxy]anilineHCID 67520675[4-({3-chloro-4-[(3-fluorobenzyl)oxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]acetic acid

生成物 1

HCID 575973913-[4-({3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}amino)-5H-pyrrolo[3,2-d]pyrimidin-5-yl]propan-1-ol

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
100 °C

実験手順

To a solution of 3-(4-chloro-5H-pyrrolo[3,2-d]pyrimidin-5-yl)propan-1-ol (201 mg) synthesized in Example 53 (ii) in isopropyl alcohol (2.5 mL) was added 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline (381 mg), and the mixture was stirred in an oil bath at a temperature of 100° C. for 2.0 hrs. The reaction mixture was allowed to cool to room temperature, diluted with 5% aqueous sodium hydrogen carbonate solution (25 mL), and extracted with ethyl acetate (30 mL×3). The organic layer was washed successively with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to basic silica gel chromatography (eluent:hexane/ethyl acetate=95/5→20/80). The object fraction was concentrated under reduced pressure and dried. Ethanol/diisopropyl ether (1/9) was added to the residue, and the mixture was stirred with heating to 80° C., allowed to cool to room temperature, and stood still. The resultant precipitate was collected by filtration. The obtained precipitate was washed with diisopropyl ether and dried under reduced pressure to give the title compound (375 mg) as white powder crystals.

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with ethyl acetate (30 mL×3)
  3. washThe organic layer was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. concentrationThe object fraction was concentrated under reduced pressure
  7. customdried
  8. additionEthanol/diisopropyl ether (1/9) was added to the residue
  9. stirringthe mixture was stirred
  10. temperaturewith heating to 80° C.
  11. temperatureto cool to room temperature
  12. filtrationThe resultant precipitate was collected by filtration
  13. washThe obtained precipitate was washed with diisopropyl ether
  14. customdried under reduced pressure

出典と根拠

ORDレコード
ord-4df3904ce94a4f039f3d52d01068a3d0
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

反応ノート

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