Sodium Hydroxide → HCID 86685996, compound

HRID 2277702Notes

Reaction equation

HRID 2277702 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[N:18]([C:24]1[CH:25]=[N:26][CH:27]=[C:28]([S:30][CH3:31])[CH:29]=1)[CH2:17][CH2:16]2.[OH-].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[N:18]([C:24]1[CH:25]=[N:26][CH:27]=[C:28]([S:30]([CH3:31])=[O:9])[CH:29]=1)[CH2:17][CH2:16]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86685997HCID 86685997, compound

Product 1

HCID 86685996HCID 86685996, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (17.3 mg, 0.1 mmol) was added into a solution of 6-chloro-2-(5-methylsulfanyl-pyridin-3-yl)-3,4-dihydro-2H-isoquinolin-1-one (example 59) (30.5 mg, 0.1 mmol) in DCM (2 mL). The reaction mixture was stirred at RT for 2 hours before it was neutralized with 5% aq. NaOH and extracted with DCM (5 mL, 2×). The organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a crude product which was then purified by prep-HPLC to give title compound (6 mg, 19%) as a white solid. MS: 321.1 (M+H+).

Workup

  1. extractionextracted with DCM (5 mL, 2×)
  2. washThe organic layers were washed with brine
  3. customdried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customto give a crude product which
  7. customwas then purified by prep-HPLC

Sources & evidence

ORD record
ord-299269531db74f00a11f2a118090232e
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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