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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
ノート
印刷プレビュー

反応式

HRID 1878040 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
2 回
HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4f64105a6a8f40f799f5d3ebe6a12d46
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08314094B2

反応ノート

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