6-(2-(3-Fluorophenyl)piperidin-1-yl)-3-nitroimidazo[1,2-b]pyridazine → 6-(2-(3-Fluorophenyl)piperidin-1-yl)imidazo[1,2-b]pyridazin-3-amine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([N+:23]([O-])=O)=[CH:21][N:22]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1>CCO>[F:1][C:2]1[CH:3]=[C:4]([CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][N:9]2[C:14]2[CH:15]=[CH:16][C:17]3[N:18]([C:20]([NH2:23])=[CH:21][N:22]=3)[N:19]=2)[CH:5]=[CH:6][CH:7]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of 6-(2-(3-fluorophenyl)piperidin-1-yl)-3-nitroimidazo[1,2-b]pyridazine (50 mg, 0.146 mmol) and SnCl2 dihydrate (165 mg, 0.732 mmol) in 5 mL EtOH was first stirred at 70° C. for 30 minutes, then cooled to ambient temperature and concentrated. EtOAc and water (10 mL each) were added to the solid residue, followed by Na2CO3 aqueous solution (2 mL×2 N) to obtain a phase break. The organic layer was separated, and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers was dried with Na2SO4 and concentrated to provide the product for the next step.
Workup
- temperaturecooled to ambient temperature
- concentrationconcentrated
- additionEtOAc and water (10 mL each) were added to the solid residue
- customto obtain a phase break
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with EtOAc (3×10 mL)
- dry with materialThe combined organic layers was dried with Na2SO4
- concentrationconcentrated
- customto provide the product for the next step
Sources & evidence
- ORD record
- ord-03b235e856db4fadb45b9722da38e36a
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450322B2
Reaction notes
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