Phenyl chloroformate → HCID 9893095、化合物

HRID 380167ノート

反応式

HRID 380167 の反応式
[NH2:1][C:2]1[C:3](=[O:24])[N:4]([CH2:20][CH2:21][CH2:22][CH3:23])[C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)=[CH:9][CH:8]=[CH:7][N:6]=2.[C:25](Cl)(=O)[O:26]C1C=CC=CC=1.[CH:35]([C:38]1[CH:44]=[CH:43][CH:42]=[C:41]([CH:45]([CH3:47])[CH3:46])[C:39]=1[NH2:40])([CH3:37])[CH3:36]>O1CCCC1.CN(C)C1C=CN=CC=1.O.CN(C)C=O>[CH2:20]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][N:6]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=2)=[C:2]([NH:1][C:25]([NH:40][C:39]2[C:38]([CH:35]([CH3:37])[CH3:36])=[CH:44][CH:43]=[CH:42][C:41]=2[CH:45]([CH3:47])[CH3:46])=[O:26])[C:3]1=[O:24])[CH2:21][CH2:22][CH3:23]

参加物

8

反応物 3

HCID 15891Phenyl chloroformateHCID 32484DiisopropylanilineHCID 11232543HCID 11232543、化合物

生成物 1

HCID 9893095HCID 9893095、化合物

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
45 °C

実験手順

To a solution of 3-amino-1-butyl-4-(3-methoxyphenyl)-1,2-dihydro-2-oxo-1,8-naphthyridine (1.70 g, 5.26 mmol) in tetrahydrofuran (14 ml) was added phenyl chlorocarbonate (1.32 ml, 10.5 ml), and the mixture was stirred at 40-50° C. for 3 hours. The mixture was allowed to cool, and thereto was added water, and the mixture was extracted with water. The extract was washed with a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in dimethylformamide (10 ml), and thereto was added a solution of 2,6-diisopropylaniline (1.24 g, 6.31 mmol) and dimethylformamide (5 ml) and 4-dimethylaminopyridine (0.62 g, 5.26 mmol), and the mixture was stirred at room temperature for one hour. To the reaction solution was added water, and the mixture was extracted with ethyl acetate. The extract was washed successively with a 5% aqueous sodium hydrogen carbonate solution and a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate to give the title compound (1.75 g, 3.32 mmol) as colorless crystals.

後処理

  1. temperatureto cool
  2. extractionthe mixture was extracted with water
  3. washThe extract was washed with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in dimethylformamide (10 ml)
  7. stirringthe mixture was stirred at room temperature for one hour
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe extract was washed successively with a 5% aqueous sodium hydrogen carbonate solution
  10. dry with materiala 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was crystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ee69487bca304e8ca588693973688bc3
出典データセット
uspto-grants-2001_10
特許番号
US06300500B1

反応ノート

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