Réaction #73072

Équation de réaction

Potassium phthalimide

1-{[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol

potassium phthalimide

→

2-({4-amino-1-[(1-hydroxycyclohexyl)methyl]-1H-imidazo[4,5-c]quinolin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction was stirred for an additional five hours
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   AutreThe residue was triturated with methanol
5. 5
   Autrethe resulting white solid was isolated by filtration
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   Autrethe residue was triturated with methanol
8. 8
   Autreto afford additional white solid
9. 9
   Autrewhich was isolated by filtration

Mode opératoire

Potassium phthalimide (2.59 g, 14.0 mmol) was added to a solution of 1-{[4-amino-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}cyclohexanol (5.07 g, 13.3 mmol) in DMF (50 mL), and the reaction mixture was stirred at room temperature overnight. An analysis by HPLC indicated the presence of starting material, and additional potassium phthalimide (1 g) was added. The reaction was stirred for an additional five hours, and then concentrated under reduced pressure. The residue was triturated with methanol, and the resulting white solid was isolated by filtration. The filtrate was concentrated under reduced pressure, and the residue was triturated with methanol to afford additional white solid, which was isolated by filtration. The two solids were combined to provide 2-({4-amino-1-[(1-hydroxycyclohexyl)methyl]-1H-imidazo[4,5-c]quinolin-2-yl}methyl)-1H-isoindole-1,3(2H)-dione.

Source