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Dimethyl Sulfoxide → 6-Methoxy-7-(2-methoxyethoxy)4-(5-(2-morpholinoethylaminosulphonyl)oxindol-3-yl)quinazoline hydrochloride

HRID 1386329
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Reaktionsgleichung

Reaktionsgleichung von HRID 1386329
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][S:10]([C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][C:17](=[O:22])[CH2:16]3)(=[O:12])=[O:11])[CH2:3][CH2:2]1.[H-].[Na+].[Cl:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([O:38][CH2:39][CH2:40][O:41][CH3:42])=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][N:27]=1.CS(C)=O>CN(C=O)C>[ClH:25].[CH3:37][O:36][C:33]1[CH:34]=[C:35]2[C:30](=[CH:31][C:32]=1[O:38][CH2:39][CH2:40][O:41][CH3:42])[N:29]=[CH:28][N:27]=[C:26]2[CH:16]1[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([S:10]([NH:9][CH2:8][CH2:7][N:4]3[CH2:5][CH2:6][O:1][CH2:2][CH2:3]3)(=[O:12])=[O:11])[CH:14]=2)[NH:18][C:17]1=[O:22]
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Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 107306534-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazolineHCID 217173035-(2-Morpholinoethylaminosulphonyl)oxindole

Produkt 1

HCID 217172136-Methoxy-7-(2-methoxyethoxy)4-(5-(2-morpholinoethylaminosulphonyl)oxindol-3-yl)quinazoline hydrochlorideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of 5-(2-morpholinoethylaminosulphonyl)oxindole (363 mg, 1.1 mmol) in DMF (3 ml) was added dropwise to a suspension of sodium hydride (89 mg, 2.2 mmol, prewashed with hexane) and the mixture stirred for 30 minutes at ambient temperature. 4-Chloro-6-methoxy-7-(2-methoxyethoxy)quinazoline (100 mg, 0.37 mmol), (prepared as described for the starting material in Example 2), was added and the mixture heated at 50° C. for 30 minutes. DMF (5 ml) and DMSO (1.5 ml) were added and the mixture heated at 60° C. for 45 minutes, the volatiles were removed by evaporation and the residue was partitioned between methylene chloride and saturated aqueous ammonium chloride solution. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/acetonitrile/methanol (60/35/5 followed by 60/30/10). The purified product was triturated with ether, collected by filtration and dried under vacuum. The solid was dissolved in methylene chloride/methanol and SM ethereal hydrogen chloride (1.5 ml) was added. The mixture was stirred for 30 minutes at ambient temperature, the volatiles were removed by evaporation and the solid residue was triturated with ether, collected by filtration and dried under vaccum to give 6-methoxy-7-(2-methoxyethoxy)4-(5-(2-morpholinoethylaminosulphonyl)oxindol-3-yl)quinazoline hydrochloride (110 mg, 46%).

Aufarbeitung

  1. additionwas added
  2. temperaturethe mixture heated at 50° C. for 30 minutes
  3. temperaturethe mixture heated at 60° C. for 45 minutes
  4. customthe volatiles were removed by evaporation
  5. customthe residue was partitioned between methylene chloride and saturated aqueous ammonium chloride solution
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation
  10. customThe residue was purified by column chromatography
  11. washeluting with methylene chloride/acetonitrile/methanol (60/35/5 followed by 60/30/10)
  12. customThe purified product was triturated with ether
  13. filtrationcollected by filtration
  14. customdried under vacuum
  15. dissolutionThe solid was dissolved in methylene chloride/methanol
  16. additionSM ethereal hydrogen chloride (1.5 ml) was added
  17. stirringThe mixture was stirred for 30 minutes at ambient temperature
  18. customthe volatiles were removed by evaporation
  19. customthe solid residue was triturated with ether
  20. filtrationcollected by filtration
  21. customdried under vaccum

Quellen und Nachweise

ORD-Eintrag
ord-000b5bceac3f487ea432bf801b9d95e5
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06265411B1

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