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 69024Notes

Reaction equation

HRID 69024 reaction equation
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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9994e1a92f7944fbaf70aabf1aaddbbe
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

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