Ammonium Hydroxide → 5-(2-Propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide
Reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([O:23]CC)=O)[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3].C([O-])(=O)C.[NH4+:30].[OH-].[NH4+]>>[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][CH2:20][C:21]([NH2:30])=[O:23])[C:6]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:9]=[CH:8][C:7]=2[N:16]=1)[CH2:2][CH3:3]Participants
4
Conditions
- Temperature
- 130 °C
Procedure
Ethyl 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanoate (5.4 g, 15.9 mmol), prepared as described in Parts A through C of Example 34) and ammonium acetate (11.0 g, 143 mmol) were sealed in a high-pressure vessel and heated for two days at 130° C. and then allowed to cool to ambient temperature. Ammonium hydroxide was added to adjust the mixture to a neutral pH. The mixture was then extracted with dichloromethane, and the combined extracts were washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 2.8 g of 5-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)pentanamide, which was combined with material from another run.
Workup
- customwere sealed in a high-pressure vessel
- temperatureto cool to ambient temperature
- extractionThe mixture was then extracted with dichloromethane
- washthe combined extracts were washed with saturated aqueous sodium bicarbonate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1f0a313931fb4679916cf002df56d581
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697873B2
Reaction notes
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