Reaction #73072

Reaction equation

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

Solvents

DMF

Conditions

Workup

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
   OtherThe residue was triturated with methanol
5. 5
   Otherthe resulting white solid was isolated by filtration
6. 6
   ConcentrationThe filtrate was concentrated under reduced pressure
7. 7
   Otherthe residue was triturated with methanol
8. 8
   Otherto afford additional white solid
9. 9
   Otherwhich was isolated by filtration

Procedure

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