HCID 11624063, compound → HCID 11501395, compound

HRID 1783663Notes

Reaction equation

HRID 1783663 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[CH:7]([N:10]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)[C:17]2[C:12](=[CH:13][C:14](SC)=[CH:15][CH:16]=2)[C:11]1=[O:29])([CH3:9])[CH3:8].O1CCOC[CH2:31]1.O>O>[CH:7]([N:10]1[N:19]=[C:18]([NH:20][C:21]2[CH:25]=[C:24]([CH3:26])[NH:23][N:22]=2)[C:17]2[C:12](=[CH:13][C:14]([S:3]([CH3:31])(=[O:5])=[O:2])=[CH:15][CH:16]=2)[C:11]1=[O:29])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 11624063HCID 11624063, compoundHCID 218864351,4-Dioxane--water (1/1)HCID 23707502Potassium hydroxy sulfite

Product 1

HCID 11501395HCID 11501395, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (0.88 g, 1.4 mmol) was added in one portion to a stirred solution of 2-iso-propyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-methylsulfanyl-2H-phthalazin-1-one (0.12 g, 0.36 mmol) in a 4:1 mixture of dioxane/water (1.2 ml) and the reaction mixture was stirred at RT for one hour. The reaction mixture was diluted with water (5 ml) and the solution was extracted with EtOAc (3×75 ml), the organic layers were combined, dried (MgSO4), filtered and concentrated under vacuum to give a dark brown solid. Flash column chromatography (elution: 96% DCM, 4% MeOH) gave the title compound (0.032 g, 25% yield) as a light yellow solid (Example H-2). 1H-NMR: (400 MHz, D6-DMSO) 11.99 (1H, br s), 9.44 (1H, s), 8.76-8.68 (2H, m), 8.39 (1H, d), 6.36 (1H, s), 5.32-5.18 (1H, m), 3.36 (3H, s), 2.25 (3H, s), 1.34 (6H, d) MS (ESI+)=(M+H)+ 362.16.

Workup

  1. extractionthe solution was extracted with EtOAc (3×75 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a dark brown solid
  6. washFlash column chromatography (elution: 96% DCM, 4% MeOH)

Sources & evidence

ORD record
ord-385fb057eda2459ba0712eb41836fdce
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

Loading…