Reaction equation
[C:1](OC)(OC)(OC)[CH2:2][CH2:3][CH3:4].Cl.N1C=CC=CC=1.[NH2:18][C:19]1[CH:20]=[N:21][C:22]2[C:27]([C:28]=1[NH:29][CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])=[CH:26][CH:25]=[C:24]([Br:35])[CH:23]=2>C1(C)C=CC=CC=1>[Br:35][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[N:29]([CH2:30][C:31]([CH3:34])([OH:33])[CH3:32])[C:1]([CH2:2][CH2:3][CH3:4])=[N:18][C:19]=3[CH:20]=[N:21][C:22]=2[CH:23]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Trimethyl orthobutyrate (11.61 mL, 72.6 mmol) and catalytic pyridine hydrochloride were added to a solution of 1-(3-amino-7-bromoquinolin-4-ylamino)-2-methylpropan-2-ol (22.51 g, 72.6 mmol) in anhydrous toluene (120 mL), and the reaction was heated at reflux for two hours. The solvent was removed under reduced pressure, and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed under reduced pressure until a precipitate began to form. Hexanes were added, and the precipitate was isolated by filtration to provide 20.17 g of 1-(7-bromo-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol.
Workup
- temperaturethe reaction was heated
- temperatureat reflux for two hours
- customThe solvent was removed under reduced pressure
- dissolutionthe residue was dissolved in dichloromethane
- washwashed with water
- customThe dichloromethane was removed under reduced pressure until a precipitate
- customto form
- customthe precipitate was isolated by filtration
Sources & evidence
- ORD record
- ord-dd064fe13c304d048f8985c83af1053f
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091214B2
Linked notes
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