Sodium Bicarbonate → 6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolin-4-one

HRID 454127Notes

Reaction equation

HRID 454127 reaction equation
BrC1C=CC([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=C(F)C=1.C(=O)([O-])O.[Na+]>Cl>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH2:20][CH2:21][CH2:22][N:23]([CH3:28])[S:24]([CH3:27])(=[O:26])=[O:25])[N:10]=[CH:9][NH:8][C:7]2=[O:6]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 220307614-(4-Bromo-2-fluorophenoxy)-6-methoxy-7-(3-(N-methyl N-methylsulphonylamino)propoxy)quinazoline

Product 1

HCID 1357631136-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolin-4-oneYield 104%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-(4-Bromo-2-fluorophenoxy)-6-methoxy-7-(3-(N-methyl N-methylsulphonylamino)propoxy)quinazoline (4.70 g, 9.1 mmol) was dissolved in 2N aqueous hydrochloric acid solution (85 ml) and heated at reflux for 1 hour. After cooling, the solution was carefully poured into saturated aqueous sodium hydrogen carbonate solution (to pH8) and stirred vigorously for 30 minutes. The resulting precipitate was filtered and dried. The filter cake was then taken up as a suspension in acetone, filtered, washed with diethyl ether and dried to give 6-methoxy-7-(3-(N-methyl-N-methylsulphonylamino)propoxy)quinazolin-4-one (3.23 g, 88%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. temperatureAfter cooling
  4. filtrationThe resulting precipitate was filtered
  5. customdried
  6. filtrationfiltered
  7. washwashed with diethyl ether
  8. customdried

Sources & evidence

ORD record
ord-c51054c7787c47e4baac115ed5f94ea1
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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