HCID 18753448, compound → HCID 22478248, compound

HRID 1838558Notes

Reaction equation

HRID 1838558 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:32]=[CH:31][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][S:28][CH2:29][CH3:30])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1>O.CO>[Br:7][C:8]1[CH:32]=[CH:31][C:11]([NH:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH2:26][CH2:27][S:28]([CH2:29][CH3:30])=[O:1])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1

Participants

5

Reactant 2

HCID 18753448HCID 18753448, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 22478248HCID 22478248, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of OXONE, (trade mark of E.I. du Pont de Nemours & Co.,Inc), (150 mg) in water (2 ml) was added to a solution of 4-(4-bromo-2-fluoroanilino)-7-(2-ethylthioethoxy)-6-methoxyquinazoline (125 mg, 0.28 mmol), (prepared as described in Example 24), in methanol (10 ml). The reaction mixture was stirred for 16 hours at ambient temperature, the methanol was removed by evaporation, the aqueous residue was basified with sodium hydrogen carbonate solution and then extracted with ethyl acetate (3×30 ml). The extracts were combined, washed with water (×2), and then brine, and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by column chromatography eluting with ethyl acetate and then with methylene chloride/methanol (9/1) to give 4-(4-bromo-2-fluoroanilino)-7-(2ethylsulphinylethoxy)-6methoxyquinazoline (32 mg, 31%).

Workup

  1. customthe methanol was removed by evaporation
  2. extractionextracted with ethyl acetate (3×30 ml)
  3. washwashed with water (×2)
  4. dry with materialbrine, and dried (MgSO4)
  5. customThe solvent was removed by evaporation
  6. customthe residue was purified by column chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-e331805852264c749f3a43fe22953061
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Reaction notes

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