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1-Naphthol → 6-Methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline

HRID 1791521
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HRID 1791521 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([OH:40])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:40][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1
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참가 물질

6

반응물 4

HCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

생성물 1

HCID 220306666-Methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline수율 65%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 1-naphthol (111 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40 ml) and stirred at ambient temperature for a few minutes. The reaction mixture was extracted with ethyl acetate and the organic extracts were washed with water. The organic extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give a solid which was triturated with ether, filtered and dried to give 6-methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline (194 mg, 65%).

후처리

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. stirringstirred at ambient temperature for a few minutes
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic extracts were washed with water
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with methylene chloride/methanol (95/5)
  10. customto give a solid which
  11. customwas triturated with ether
  12. filtrationfiltered
  13. customdried

출처 및 근거

ORD 기록
ord-8f09a10886004035a4e54b16cdcc6b3a
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07074800B1

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