Hydrochloric Acid → 1-methyl-6-{3-[N-(1-oxo-1,2-dihydroisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one

HRID 69024ノート

反応式

HRID 69024 の反応式
C[O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([N:13]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][CH:34]=2)[N:31]([CH3:35])[C:30](=[O:36])[CH:29]=[CH:28]3)[CH2:14][C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:5][N:4]=1.Cl.[OH-].[Na+]>C(O)C>[CH3:35][N:31]1[C:32]2[C:27](=[CH:26][C:25]([O:24][CH2:23][CH2:22][CH2:21][N:13]([C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:3](=[O:2])[NH:4][CH:5]=3)[CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[CH:34][CH:33]=2)[CH:28]=[CH:29][C:30]1=[O:36]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 867626926-{3-[N-(1-Methoxyisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-one

生成物 1

HCID 867626911-methyl-6-{3-[N-(1-oxo-1,2-dihydroisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one収率 38.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
75 °C

実験手順

6-{3-[N-(1-Methoxyisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-one (55 mg) was added to a 1N-hydrogen chloride in ethanol solution (5 ml), and stirred at 75° C. for 2 hours. The reaction mixture was cooled to room temperature. 1N-Sodium hydroxide aqueous solution (5 ml) was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (20.6 mg) as a colorless oil.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customcondensed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1)
  6. customcondensed under reduced pressure

出典と根拠

ORDレコード
ord-9994e1a92f7944fbaf70aabf1aaddbbe
出典データセット
uspto-grants-2014_09
特許番号
US08822453B2

反応ノート

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