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

HRID 1386337
Notes
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Reaction equation

HRID 1386337 reaction equation
[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][CH3:39])=[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][CH3:39])[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 27693644-Chloro-6,7-dimethoxyquinazolineHCID 217173035-(2-Morpholinoethylaminosulphonyl)oxindole

Product 1

HCID 217171756,7-Dimethoxy-4-(5-(2-morpholinoethylaminosulphonyl)oxindol-3-yl)quinazoline hydrochlorideYield 52.1%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 5-(2-morpholinoethylaminosulphonyl)oxindole (364 mg, 1.1 mmol), (prepared as described for the starting material in Example 48), in DMF (3.5 ml) was added dropwise to a suspension of sodium hydride (90 mg, 2.2 mmol, prewashed with hexane) in DMF (1.5 ml). The mixture was stirred for 30 minutes at ambient temperature and 4-chloro-6,7dimethoxyquinazoline (84 mg, 0.37 mmol), (prepared as described for the starting material in Example 1), was added as a solid followed by DMSO (2 ml). The mixture was stirred for 45 minutes at 60° C., allowed to cool and 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/methanol (95/5 followed by 92/8). The purified solid was triturated with ether, collected by filtration; washed with ether and dried under vacuum. The solid was dissolved in methylene chloride/methanol and 2M ethereal hydrogen chloride (1 ml) was added. The volatiles were removed bv evaporation, the solid residue triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 6,7-dimethoxy-4-(5-(2-morpholinoethylaminosulphonyl)oxindol-3-yl)quinazoline hydrochloride (106 mg, 50%).

Workup

  1. additionwas added as a solid
  2. stirringThe mixture was stirred for 45 minutes at 60° C.
  3. temperatureto cool
  4. custompartitioned between methylene chloride and saturated aqueous ammonium chloride solution
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by column chromatography
  10. washeluting with methylene chloride/methanol (95/5 followed by 92/8)
  11. customThe purified solid was triturated with ether
  12. filtrationcollected by filtration
  13. washwashed with ether
  14. customdried under vacuum
  15. dissolutionThe solid was dissolved in methylene chloride/methanol
  16. addition2M ethereal hydrogen chloride (1 ml) was added
  17. customThe volatiles were removed
  18. custombv evaporation
  19. customthe solid residue triturated with ether
  20. filtrationcollected by filtration
  21. washwashed with ether
  22. customdried under vacuum

Sources & evidence

ORD record
ord-e915b0e2ce2d40e193eecabf2548cefc
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06265411B1

Reaction notes

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