Trifluoroacetic acid → 2,2-Bis-hydroxymethyl-3-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-propan-1-ol

HRID 228989ノート

反応式

HRID 228989 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[C:16]([CH3:25])=[N:17][C:18]2[C:23]([CH:24]=1)=[CH:22][CH:21]=[CH:20][CH:19]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][C:34]([CH2:39][OH:40])([CH2:37][OH:38])[CH2:35][OH:36].FC(F)(F)C(O)=O.[OH-].[Na+]>O.CN(C)C=O>[OH:36][CH2:35][C:34]([CH2:39][OH:40])([CH2:33][O:13][C:12]1[CH:11]=[C:10]2[C:5]([C:6]([O:14][C:15]3[C:16]([CH3:25])=[N:17][C:18]4[C:23]([CH:24]=3)=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:2][CH3:1])[CH2:37][OH:38]

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 879541,3-Propanediol, 2-(bromomethyl)-2-(hydroxymethyl)-HCID 1358548286-Methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol2 回

生成物 1

HCID 577564442,2-Bis-hydroxymethyl-3-[6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-yloxy]-propan-1-ol収率 21%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

N,N-Dimethylformamide (1.5 ml) was added to 6-methoxy-4-(2-methyl-quinolin-3-yloxy)-quinolin-7-ol (compound 352) (50 mg), potassium carbonate (62 mg), and 2-bromomethyl-2-hydroxymethyl-propane-1,3-diol (90 mg), and the mixture was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was dissolved in dichloromethane (3 ml) to prepare a solution. Trifluoroacetic acid (3 ml) was added dropwise to the solution at 0° C., and the mixture was then stirred at room temperature for 3 hr. The reaction solution was made alkaline by the addition of a 1 N aqueous sodium hydroxide solution and was extracted with chloroform. The chloroform layer was washed with water and was then dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by thin layer chromatography using chloroform-methanol to give the title compound (14 mg, yield 21%).

後処理

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. dissolutionthe residue was dissolved in dichloromethane (3 ml)
  7. customto prepare a solution
  8. stirringthe mixture was then stirred at room temperature for 3 hr
  9. extractionwas extracted with chloroform
  10. washThe chloroform layer was washed with water
  11. dry with materialwas then dried over anhydrous sodium sulfate
  12. customThe solvent was removed by distillation under the reduced pressure
  13. customthe residue was purified by thin layer chromatography

出典と根拠

ORDレコード
ord-42f744f4d1844e79a641dce6153fc873
出典データセット
uspto-grants-2009_07
特許番号
US07560558B2

反応ノート

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