Sodium Hydroxide → 2-[4-(3-Methylamino-piperidin-1-yl)-phenyl]-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-2H-isoquinolin-1-one

HRID 69491Notes

Reaction equation

HRID 69491 reaction equation
[CH3:1][N:2]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH2:29][C@@H:30]5[CH2:34][CH2:33][CH2:32][O:31]5)[CH:24]=4)[C:19]3=[O:35])=[CH:14][CH:13]=2)[CH2:7]1)C(=O)C.[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:1][NH:2][CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[C:23]([O:28][CH2:29][C@@H:30]5[CH2:34][CH2:33][CH2:32][O:31]5)[CH:24]=4)[C:19]3=[O:35])=[CH:14][CH:13]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57916875N-methyl-N-[1-(4-{1-oxo-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-1H-isoquinolin-2-yl}-phenyl)-piperidin-3-yl]-acetamide

Product 1

HCID 579167212-[4-(3-Methylamino-piperidin-1-yl)-phenyl]-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-2H-isoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of N-methyl-N-[1-(4-{1-oxo-6-[(S)-1-(tetrahydrofuran-2-yl)methoxy]-1H-isoquinolin-2-yl}-phenyl)-piperidin-3-yl]-acetamide (552 mg) was stirred in 20% sulfuric acid (with methanol as solubilizing agent) for 16 h at 90° C. The mixture was neutralized with 2N NaOH, extracted with dichloromethane, dried over magnesium sulfate and concentrated. The residue was purified by preparative HPLC. In this way the product was obtained with molecular weight 433.56 (C26H31N3O3); MS (ESI): 434 (M+H+).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by preparative HPLC
  5. customIn this way the product was obtained with molecular weight 433.56 (C26H31N3O3)

Sources & evidence

ORD record
ord-27f10a5e0f7143eaaa831baff2736e28
Source dataset
uspto-grants-2014_09
Patent number
US08822495B2

Reaction notes

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