Dichloromethane → 7-(3-methyl-2-oxotetrahydropyrimidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1162931ノート

反応式

HRID 1162931 の反応式
[C:1](Cl)(Cl)=[O:2].C(Cl)Cl.[CH3:8][NH:9][CH2:10][CH2:11][CH2:12][NH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])[NH:20][C:21]2=[O:24])=[CH:16][CH:15]=1.C(N(CC)CC)C>O>[CH3:8][N:9]1[CH2:10][CH2:11][CH2:12][N:13]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:33])([F:34])[F:32])[NH:20][C:21]3=[O:24])=[CH:16][CH:15]=2)[C:1]1=[O:2]

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 6371PhosgeneHCID 8471TriethylamineHCID 575581337-(3-methylaminopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

生成物 1

HCID 575579037-(3-methyl-2-oxotetrahydropyrimidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one収率 14%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Phosgene (294 μl, 0.559 mmol) was added at 0° C. to an anhydrous methylene chloride solution (2 ml) that contained the 7-(3-methylaminopropylamino)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (70 mg, 0.186 mmol) obtained in step B. The obtained mixture was stirred for 10 minutes. Thereafter, triethylamine (156 μl, 0.112 mmol) was added to the reaction solution, and the obtained mixture was then stirred for 30 minutes. Thereafter, water was added to the reaction solution. An organic layer was separated, and a water layer was then extracted with methylene chloride. The organic layer was mixed with the extract. The obtained mixture was washed with water and a saturated saline solution, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. The obtained residue was purified by amino silica gel column chromatography (methylene chloride:methanol=40:1), so as to obtain 7-(3-methyl-2-oxotetrahydropyrimidin-1-yl)-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one (10.2 mg, 14%).

後処理

  1. stirringthe obtained mixture was then stirred for 30 minutes
  2. customAn organic layer was separated
  3. extractiona water layer was then extracted with methylene chloride
  4. additionThe organic layer was mixed with the extract
  5. washThe obtained mixture was washed with water
  6. dry with materiala saturated saline solution, and was then dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled away under reduced pressure
  8. customThe obtained residue was purified by amino silica gel column chromatography (methylene chloride:methanol=40:1)

出典と根拠

ORDレコード
ord-1ec3d0687496447fa0a81e3669038f02
出典データセット
uspto-grants-2010_10
特許番号
US07820693B2

反応ノート

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