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

HRID 1878040
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HRID 1878040 반응식
[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]
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 962
Water
용매
2회
HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4f64105a6a8f40f799f5d3ebe6a12d46
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08314094B2

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