1,4-Dioxane--water (1/1) → HCID 24753867, compound

HRID 1783727Notes

Reaction equation

HRID 1783727 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]([CH2:27]SC)=[CH:15][CH:16]=2)[C:11]1=[O:30])([CH3:9])[CH3:8].O1CCOC[CH2:32]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]([CH2:27][S:3]([CH3:32])(=[O:5])=[O:2])=[CH:15][CH:16]=2)[C:11]1=[O:30])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 218864351,4-Dioxane--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 24753866HCID 24753866, compound

Product 1

HCID 24753867HCID 24753867, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Oxone (0.43 g, 0.7 mmol) was added in one portion to a stirred solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-methylsulfanylmethyl-2H-phthalazin-1-one (0.06 g, 0.17 mmol) in a 4:1 mixture of dioxane/water (1.2 ml) and the reaction mixture was stirred at RT for 1 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 the title compound (0.013 g, 20% yield) as a white solid. δH (400 MHz, DMSO) 9.23 (1H, s), 8.48 (1H, d), 8.38 (1H, d), 7.89 (1H, dd), 6.36 (1H, s), 5.33-5.20 (1H, m), 4.77 (2H, s), 2.96 (3H, s), 2.25 (3H, s), 1.33 (6H, d) Tr=1.58 min, m/z (ES+) (M+H)+ 376.24.

Workup

  1. extractionthe solution was extracted with EtOAc (3×75 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d984914711904b51b3b77f5ad24366d3
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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