Potassium Carbonate → 4-methoxy-1-(tetrahydro-2H-pyran-4-yl)-1,2-dihydro-3H-pyrazolo[4,3-c]pyridin-3-one
Reaction equation
I[C:2]1[C:7]([C:8]([NH:10][NH:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:18][CH3:19])[N:5]=[CH:4][CH:3]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CS(C)=O.[Cu]I>[CH3:19][O:18][C:6]1[C:7]2[C:8](=[O:9])[NH:10][N:11]([CH:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[C:2]=2[CH:3]=[CH:4][N:5]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 4-iodo-2-methoxy-N′-(tetrahydro-2H-pyran-4-yl)nicotinohydrazide (500 mg), L-proline (30.5 mg), potassium carbonate (366 mg) and copper(I) iodide (25.2 mg) in DMSO (25 mL) was stirred overnight at room temperature under nitrogen atmosphere. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (223 mg).
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-a07e1aca27ed461f99355f6e8b2ef8f8
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09371320B2
Reaction notes
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