Sulfuric Acid → 1-{3-[7-(3-Hydroxy-2-hydroxymethyl-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone

HRID 228998노트

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HRID 228998 반응식
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([C:23](=[O:25])[CH3:24])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:26][CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1(C)[O:53][CH2:52][CH:51]([CH2:54]O)[CH2:50][O:49]1.CCOC(/N=N/C(OCC)=O)=O.S(=O)(=O)(O)O.[OH-].[Na+]>O1CCCC1.O>[OH:49][CH2:50][CH:51]([CH2:52][OH:53])[CH2:54][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[C:14]([C:23](=[O:25])[CH3:24])=[N:15][C:16]4[C:21]([CH:22]=3)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[O:26][CH3:27]

참가 물질

9

반응물 6

HCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 3584869(2,2-Dimethyl-1,3-dioxan-5-yl)methanolHCID 5462977Diethyl azodicarboxylateHCID 136131623HCID 136131623, 화합물2회

생성물 1

HCID 577564981-{3-[7-(3-Hydroxy-2-hydroxymethyl-propoxy)-6-methoxy-quinolin-4-yloxy]-quinolin-2-yl}-ethanone수율 75.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

1-[3-(7-Hydroxy-6-methoxy-quinolin-4-yloxy)-quinolin-2-yl]-ethanone (compound 390) (50 mg) was dissolved in tetrahydrofuran (1 ml) to prepare a solution. Triphenylphosphine (73 mg), (2,2-dimethyl-[1,3]dioxan-5-yl)-methanol (24 mg), and diethylazodicarboxylate (0.05 ml) were added to the solution, and the mixture was stirred at room temperature for 4 hr. Further, 1 N sulfuric acid (3 ml) was added thereto, and the mixture was stirred at room temperature overnight. The reaction solution was brought to 0° C. and was stirred. The reaction solution was made alkaline by the addition of a 10% aqueous sodium hydroxide solution. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate 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 (47 mg, yield 75%).

후처리

  1. customto prepare a solution
  2. stirringthe mixture was stirred at room temperature overnight
  3. customwas brought to 0° C.
  4. stirringwas stirred
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was then 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-5440563cc4f1419cb962a95689fd5eae
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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