Methyl morpholine oxide → HCID 178515277, compound

HRID 449957Notes

Reaction equation

HRID 449957 reaction equation
C([N:4]1[C:28](=O)[C:7]2=[N:8][N:9]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[CH:26][CH:25]=[N:24]4)=[CH:19][CH:18]=3)C3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]2=[N:5]1)C=C.C[N+]1([O-])CCOCC1.I([O-])(=O)(=O)=O.[Na+].[C:44](=[O:47])(O)[O-].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O.O>[N:23]1([C:20]2[CH:19]=[CH:18][C:17]([CH2:16][N:9]3[C:44](=[O:47])[C:28]4=[N:4][NH:5][C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:6]=5[C:7]4=[N:8]3)=[CH:22][CH:21]=2)[CH:27]=[CH:26][CH:25]=[N:24]1

Participants

8

Reactant 4

HCID 82029Methyl morpholine oxideHCID 516892Sodium BicarbonateHCID 23667635Sodium periodateHCID 46897482Allyl-5-[4-(1H-pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one

Product 1

HCID 178515277HCID 178515277, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Prop-2-en-1-yl-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one [(Example 10), 209 mg, 0.547 mmol], N-methylmorpholine oxide (192 mg, 1.64 mmol, 3.0 equiv), osmium(VIII)tetraoxide (69.5 mg, 0.273 mmol, 0.5 equiv) and sodium periodate (292 mg, 1.37 mmol, 2.5 equiv) were combined in dioxane (10 mL) and water (1 mL) and placed into an oil bath preheated to 60° C. for 18 hours. The mixture was cooled to ambient temperature, poured into sodium bicarbonate (20 mL, aqueous saturated) and extracted with ethyl acetate (3×25 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol), providing the titled compound.

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. dry with materialThe combined organic extracts were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)

Sources & evidence

ORD record
ord-99e21b0d5a8443b99352356f0677a72d
Source dataset
uspto-grants-2013_07
Patent number
US08486946B2

Reaction notes

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