Water → 3-[6-Methoxy-4-(2-methyl-[1,6]naphthyridin-3-yloxy)-quinolin-7-yloxy]-propane-1,2-diol

HRID 229012노트

반응식

HRID 229012 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]1[CH2:17][O:16]1)[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[C:20]([CH3:29])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[CH:24][CH:23]=2.FC(F)(F)C(O)=[O:33].[OH-].[Na+].O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH:15]([OH:33])[CH2:17][OH:16])[N:9]=[CH:8][CH:7]=[C:6]2[O:18][C:19]1[C:20]([CH3:29])=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][N:25]=[CH:24][CH:23]=2

참가 물질

6

반응물 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 230783583-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-2-methyl-[1,6]naphthyridine

생성물 1

HCID 230782493-[6-Methoxy-4-(2-methyl-[1,6]naphthyridin-3-yloxy)-quinolin-7-yloxy]-propane-1,2-diol수율 15%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

3-(6-Methoxy-7-oxiranylmethoxy-quinolin-4-yloxy)-2-methyl-[1,6]naphthyridine (44 mg) was dissolved in methylene chloride (2 ml) to prepare a solution which was brought to 0° C. Trifluoroacetic acid (0.4 ml) was added thereto, and the mixture was stirred at 0° C. for 30 min and then at room temperature for 4 hr. The reaction solution was brought to 0° C., was stirred, and was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added thereto, and the mixture was extracted with chloroform. The chloroform layer was then washed with saturated brine and was 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 (7 mg, yield 15%).

후처리

  1. customto prepare a solution which
  2. customwas brought to 0° C
  3. waitat room temperature for 4 hr
  4. customwas brought to 0° C.
  5. stirringwas stirred
  6. extractionthe mixture was extracted with chloroform
  7. washThe chloroform layer was then washed with saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was removed by distillation under the reduced pressure
  10. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-6e3d86e8e07f4b1785b641a51d6e2340
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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