Water → (S)-7-(6-ethoxy-2,4-dimethylpyridin-3-yl)-1-(tetrahydrofuran-3-yl)-1H-pyrazolo[4,3-c]quinolin-4(5H)-one
Reaction equation
[CH2:1]([O:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[N:21]([C@H:22]4[CH2:26][CH2:25][O:24][CH2:23]4)[N:20]=[CH:19][C:18]=3[C:27]([O:29]CC)=O)=[C:13]([N+:32]([O-])=O)[CH:12]=2)=[C:6]([CH3:35])[CH:5]=1)[CH3:2].O>C(O)(=O)C.[Fe]>[CH2:1]([O:3][C:4]1[N:9]=[C:8]([CH3:10])[C:7]([C:11]2[CH:16]=[CH:15][C:14]3[C:17]4[N:21]([C@H:22]5[CH2:26][CH2:25][O:24][CH2:23]5)[N:20]=[CH:19][C:18]=4[C:27](=[O:29])[NH:32][C:13]=3[CH:12]=2)=[C:6]([CH3:35])[CH:5]=1)[CH3:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
Ethyl 5-[4-(6-ethoxy-2,4-dimethylpyridin-3-yl)-2-nitrophenyl]-1-[(S)-tetrahydrofuran-3-yl]-1H-pyrazole-4-carboxylate (97 mg) was dissolved in acetic acid (1 mL). Iron powder (56 mg) was added to the solution, and the mixture was stirred at 90° C. for four hours. The reaction mixture was returned to room temperature, and water (2 mL) was added to the reaction mixture. The precipitated solid was collected by filtration and washed with water. The resulting solid was dissolved in ethanol (1 mL) at 90° C. The solution was ice-cooled, and the precipitated solid was collected by filtration. The resulting solid was washed with MTBE to give the title compound (16 mg).
Workup
- customwas returned to room temperature
- filtrationThe precipitated solid was collected by filtration
- washwashed with water
- dissolutionThe resulting solid was dissolved in ethanol (1 mL) at 90° C
- temperaturecooled
- filtrationthe precipitated solid was collected by filtration
- washThe resulting solid was washed with MTBE
Sources & evidence
- ORD record
- ord-d5453378ac1b43089a507e7d2ae43811
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08563565B2
Reaction notes
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