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

HRID 1878040Notes

Reaction equation

HRID 1878040 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])[N:6]([CH3:22])[C:5]2([CH2:27][NH:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:23]([F:26])([F:25])[F:24].[N+]([O-])([O-])=O.[NH4+].[Ce].C(Cl)(Cl)Cl>C(#N)C.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:21])[N:6]([CH3:22])[C:5]2([CH2:27][NH:28][C:29](=[O:37])[C:30]1[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=1)[C:23]([F:25])([F:26])[F:24]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 57418452Ammonium cerium-nitrateHCID 68487482N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

Product 1

HCID 68489355N-{[6-bromo-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

N-{[6-bromo-1-(4-methoxybenzyl)-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (9.6 mg, 0.017 mmol) was dissolved in acetonitrile (1.0 mL) and water (0.25 mL), and cerium ammonium nitrate (27.2 mg, 0.050 mmol) was added to the reaction solution under ice-cooling. After the reaction solution was stirred at room temperature for 4 hours, chloroform and water were added thereto and the solution was stirred at room temperature. The organic layer was separated and washed with 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 thin-layer chromatography (chloroform/methanol=1/4), whereby the objective N-{[6-bromo-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (4.0 mg, 53%) was obtained as a white solid.

Workup

  1. temperaturecooling
  2. stirringthe solution was stirred at room temperature
  3. customThe organic layer was separated
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter the drying agent was removed by filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by thin-layer chromatography (chloroform/methanol=1/4), whereby the objective N-{[6-bromo-3-methyl-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl]methyl}4-fluorobenzamide (4.0 mg, 53%)
  9. customwas obtained as a white solid

Sources & evidence

ORD record
ord-4f64105a6a8f40f799f5d3ebe6a12d46
Source dataset
uspto-grants-2012_11
Patent number
US08314094B2

Reaction notes

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