7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine → 2-butyl-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]=[CH:14][C:13]3[N:19]=[C:20]([CH2:23][CH2:24][CH2:25][CH3:26])[N:21]([CH3:22])[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>>[CH2:23]([C:20]1[N:21]([CH3:22])[C:12]2[C:11]3[CH:10]=[C:9]([OH:8])[CH:18]=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:19]=1)[CH2:24][CH2:25][CH3:26]Participants
Procedure
A modification of the general method described in Part J of Example 1 was followed using 8-benzyloxy-2-butyl-1-methyl-1H-imidazo[4,5-c]quinoline (14.65 g, 42.4 mmol) in lieu of 7-benzyloxy-1-(2-methylpropyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine. The reaction was placed under hydrogen pressure for 3.5 hours. The catalyst was removed by filtration and washed with ethyl acetate. The filtrate was concentrated under reduced pressure to a small volume, and hexanes were added. A precipitate formed, and the mixture was stored overnight in a refrigerator. The solid was isolated by filtration, washed with hexanes (500 mL), and dried for three days under high vacuum to provide 9.40 g of 2-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-8-ol as a white solid, mp 219-220.2° C.
Workup
- customfor 3.5 hours
- customThe catalyst was removed by filtration
- washwashed with ethyl acetate
- concentrationThe filtrate was concentrated under reduced pressure to a small volume, and hexanes
- additionwere added
- customA precipitate formed
- customThe solid was isolated by filtration
- washwashed with hexanes (500 mL)
- customdried for three days under high vacuum
Sources & evidence
- ORD record
- ord-31af08a0371a4a9d89322e6100bbc227
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365567B2
Reaction notes
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