Sodium Pyrosulfite → N-{[6-bromo-2-oxo-4-(trifluoromethyl)-1,2, 3,4-tetrahydroquinazolin-4-yl]methyl}-4-fluorobenzamide

HRID 1878033Notes

Reaction equation

HRID 1878033 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8](CC1C=CC(OC)=CC=1)[C:7](=[O:21])[NH:6][C:5]2([CH2:26][NH:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:22]([F:25])([F:24])[F:23].[N+]([O-])([O-])=O.[NH4+].[Ce].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:21])[NH:6][C:5]2([CH2:26][NH:27][C:28](=[O:36])[C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1)[C:22]([F:25])([F:23])[F:24]

Participants

6

Reactant 3

HCID 656671Sodium PyrosulfiteHCID 57418452Ammonium cerium-nitrateHCID 68486610N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}-4-fluorobenzamide

Product 1

HCID 68488834N-{[6-bromo-2-oxo-4-(trifluoromethyl)-1,2, 3,4-tetrahydroquinazolin-4-yl]methyl}-4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of N-{[6-bromo-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}-4-fluorobenzamide (260 mg, 0.46 mmol) in acetonitrile (6 mL), an aqueous solution (1 mL) of cerium ammonium nitrate (755 mg, 1.38 mmol) was added dropwise at room temperature. The reaction solution was stirred at room temperature for 4 hours. Sodium pyrosulfite was added to the reaction solution, and the solution was stirred for 30 minutes, and then diluted with ethyl acetate and the organic layer was separated. The organic layer was washed sequentially with water and saturated brine and then dried over magnesium sulfate. After the drying agent was removed by filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1), whereby the objective compound (150 mg, 73%) was obtained as a white solid.

Workup

  1. stirringthe solution was stirred for 30 minutes
  2. customthe organic layer was separated
  3. washThe organic layer was washed sequentially with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter the drying agent was removed by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/1), whereby the objective compound (150 mg, 73%)
  8. customwas obtained as a white solid

Sources & evidence

ORD record
ord-7601f1823f774a5ea3a1dccd066bb013
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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