Methyl morpholine oxide → 5-[4-(1H-Pyrazol-1-yl)benzyl]-2,5-dihydro-3H-pyrazolo[4,3-c]cinnolin-3-one
Reaction equation
C([N:4]1[C:28](=[O:29])[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)[C:10]3[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(=O)(O)[O-].[Na+]>O1CCOCC1.[Os](=O)(=O)(=O)=O.O>[N:23]1([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][N:9]3[C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=4[C:6]4=[N:5][NH:4][C:28](=[O:29])[C:7]4=[N:8]3)=[CH:18][CH:19]=2)[CH:27]=[CH:26][CH:25]=[N:24]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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
- extractionextracted with ethyl acetate (3×25 mL)
- dry with materialThe combined organic extracts were dried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel gradient chromatography (100:0 to 90:10; dichloromethane:methanol)
Sources & evidence
- ORD record
- ord-606a503a7ac54db48fad7a8a7298d3fc
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653079B2
Reaction notes
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