Methanol → 4-(4-Bromo-2-fluoroanilino)6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline

HRID 1838562

Reaction equation

HRID 1838562 reaction equation
O[O:2][S:3]([O-:5])=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][CH2:28]SC)=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1.[CH3:34]O>O.C(Cl)Cl>[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][CH2:28][S:3]([CH3:34])(=[O:5])=[O:2])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][N:14]=2)=[C:10]([F:33])[CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 224782814-(4-Bromo-2-fluoroanilino)-6-methoxy-7-(3-methylthiopropoxy)quinazolineHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 187534474-(4-Bromo-2-fluoroanilino)6-methoxy-7-(3-methylsulphonylpropoxy)quinazolineYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of OXONE, (trade mark of E.I. du Pont de Nemours & Co.,Inc), (800 mg) in water (4.5 ml) was added to a solution of 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-methylthiopropoxy)quinazoline (300 mg, 0.66 mmol), (prepared as described in Example 31), in methanol (15 ml) and the mixture was stirred for 4 hours at ambient temperature. The mixture was diluted with methylene chloride, was washed with aqueous sodium hydrogen carbonate solution, dried (MgSO4) and the solvent was removed by evaporation. The residue was triturated with ethyl acetate/hexane, collected by filtration and dried to give 4-(4-bromo-2-fluoroanilino)-6-methoxy-7-(3-methylsulphonylpropoxy)quinazoline (235 mg, 73%).

Workup

  1. washwas washed with aqueous sodium hydrogen carbonate solution
  2. dry with materialdried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe residue was triturated with ethyl acetate/hexane
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-b2450a5c16e2458e99ab36c13258c680
Source dataset
uspto-grants-2004_01
Patent number
US06673803B2

Linked notes

Loading…