Water → HCID 24753685, compound

HRID 1783717Notes

Reaction equation

HRID 1783717 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]([S:27][CH2:28][CH2:29]SC)=[CH:15][CH:16]=2)[C:11]1=[O:32])([CH3:9])[CH3:8].O1CCOC[CH2:34]1.[OH2:39].[OH2:40]>>[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:27]([CH2:28][CH2:29][S:3]([CH3:34])(=[O:5])=[O:2])(=[O:40])=[O:39])=[CH:15][CH:16]=2)[C:11]1=[O:32])([CH3:9])[CH3:8]

Participants

5

Reactant 4

HCID 962WaterHCID 218864351,4-Dioxane--water (1/1)HCID 23707502Potassium hydroxy sulfiteHCID 24753681HCID 24753681, compound

Product 1

HCID 24753685HCID 24753685, compoundYield 57%

Procedure

Oxone (0.12 g, 0.07 mmol) was added in one portion to a stirred solution of 2-isopropyl-4-(5-methyl-1H-pyrazol-3-ylamino)-7-(2-methylsulfanyl-ethylsulfanyl)-2H-phthalazin-1-one (0.013 g, 0.03 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 (0.008 g, 57% yield) as a white solid. δH (400 MHz, DMSO) 9.69 (1H, br s), 8.75 (1H, d), 8.71 (1H, d), 8.47 (1H, dd), 6.40 (1H, s), 5.31-5.22 (1H, m), 3.95-3.89 (2H, m), 3.48-3.42 (2H, m), 3.06 (3H, s), 2.29 (3H, s), 1.36 (6H, d) Tr=1.61 min, m/z (ES+) (M+H)+ 454.10.

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-78510a8ffd544d4f98a1aa1b8f9cdba4
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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