HCID 18753448, compound → HCID 22478248, compound

HRID 547191Notes

Reaction equation

HRID 547191 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. duPont 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 chloridetmethanol (9/1) to give 4-(4-bromo-2-fluoroanilino)-7-(2-ethylsulphinylethoxy)-6-methoxyquinazoline (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-32feff0187454c62957603fc0bc2b4c1
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

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