7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 4-amino-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol
Reaction equation
C([O:8][C:9]1[CH:18]=[CH:17][C:16]2[N:15]=[C:14]([NH2:19])[C:13]3[N:20]=[C:21]([CH2:24][CH3:25])[N:22]([CH3:23])[C:12]=3[C:11]=2[CH:10]=1)C1C=CC=CC=1.C(OC1C=CC2C3N(CC(C)C)C(CCC)=NC=3C(N)=NC=2C=1)C1C=CC=CC=1>>[NH2:19][C:14]1[C:13]2[N:20]=[C:21]([CH2:24][CH3:25])[N:22]([CH3:23])[C:12]=2[C:11]2[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=2[N:15]=1Participants
3
Procedure
The general method described in Example 5 was followed using 8-benzyloxy-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-4-amine (0.47 g, 1.4 mmol), prepared as described in Example 57, in lieu of 7-benzyloxy-2-propyl-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine. The hydrogenation was complete in four hours, and after the catalyst was removed by filtration, the filtrate was concentrated under reduced pressure to a small volume. Hexanes were added, and a precipitate formed, which was isolated by filtration and washed with hexanes. The solid was recrystallized from methanol to provide 70 mg of 4-amino-2-ethyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol as a white, crystalline solid, mp>240° C.
Workup
- customprepared
- customafter the catalyst was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure to a small volume
- additionHexanes were added
- customa precipitate formed
- customwhich was isolated by filtration
- washwashed with hexanes
- customThe solid was recrystallized from methanol
Sources & evidence
- ORD record
- ord-4324bd61a850473b9c7f30e445fa408d
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07897597B2
Reaction notes
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