Methylamine → HCID 68932042, compound
Reaction equation
[CH2:1]([C:4]1[N:5]([CH2:17][CH2:18][CH2:19][C:20](OCC)=[O:21])[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].C1COCC1.[CH3:30][NH2:31]>O>[CH3:30][NH:31][C:20](=[O:21])[CH2:19][CH2:18][CH2:17][N:5]1[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]=[C:4]1[CH2:1][CH2:2][CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A mixture of ethyl 4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanoate (2.0 g, 6.1 mmol), THF (10 mL), and methylamine (available as a 40% solution in water, 4 mL, 52 mmol) was sealed in a high-pressure vessel and heated at 70° C. overnight. An analysis by TLC indicated the presence of starting material, and the reaction was sealed and heated at 80° C. for nine hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane (100 mL). The resulting solution was washed with 5% aqueous sodium hydroxide (2×25 mL), dried over potassium carbonate, filtered, and concentrated under reduced pressure to provide 1.83 g of N-methyl-4-(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butanamide.
Workup
- customwas sealed in a high-pressure vessel
- customthe reaction was sealed
- temperatureheated at 80° C. for nine hours
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was dissolved in dichloromethane (100 mL)
- washThe resulting solution was washed with 5% aqueous sodium hydroxide (2×25 mL)
- dry with materialdried over potassium carbonate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-25696d12aeb44402acec42de97a1b427
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697873B2
Reaction notes
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