Potassium Carbonate → 1-{2-[6-Methoxy-4-(2-methyl-[1,8]naphthyridin-3-yloxy)-quinolin-7-yloxy]-ethyl}-piperidin-3-ol

HRID 229002노트

반응식

HRID 229002 반응식
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([C:9]([O:15][C:16]3[C:17]([CH3:26])=[N:18][C:19]4[C:24]([CH:25]=3)=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:10][CH:11]=[N:12]2)=[CH:7][C:6]=1[O:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].[OH:35][CH:36]1[CH2:41][CH2:40][CH2:39][NH:38][CH2:37]1>CN(C)C=O>[CH3:28][O:27][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:5]=1[O:4][CH2:3][CH2:2][N:38]1[CH2:39][CH2:40][CH2:41][CH:36]([OH:35])[CH2:37]1)[N:12]=[CH:11][CH:10]=[C:9]2[O:15][C:16]1[C:17]([CH3:26])=[N:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][N:20]=2

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 232933-HydroxypiperidineHCID 577563513-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine2회

생성물 1

HCID 577565631-{2-[6-Methoxy-4-(2-methyl-[1,8]naphthyridin-3-yloxy)-quinolin-7-yloxy]-ethyl}-piperidin-3-ol수율 59.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

3-[7-(2-Chloro-ethoxy)-6-methoxy-quinolin-4-yloxy]-2-methyl-[1,8]naphthyridine (compound 398) (42 mg) was dissolved in N,N-dimethylformamide (2 ml) to prepare a solution. Potassium carbonate (44 mg) and 3-hydroxypiperidine (32 mg) were added to the solution, and the mixture was stirred at 80° C. overnight. The reaction solution was cooled to room temperature, and the solvent was removed by distillation under the reduced pressure. Water was then added to the residue, and the mixture was extracted with chloroform. The chloroform layer was 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 (29 mg, yield 56%).

후처리

  1. customto prepare a solution
  2. temperatureThe reaction solution was cooled to room temperature
  3. customthe solvent was removed by distillation under the reduced pressure
  4. additionWater was then added to the residue
  5. extractionthe mixture was extracted with chloroform
  6. washThe chloroform layer was washed with saturated brine
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customthe residue was purified by thin layer chromatography

출처 및 근거

ORD 기록
ord-8f7e365dd13643ccae9090528cc8aaf7
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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