Ammonia → 2-(ethoxymethyl)-1-[3-(3-methylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine
Reaction equation
Cl[C:2]1[C:11]2[N:12]=[C:13]([CH2:24][O:25][CH2:26][CH3:27])[N:14]([CH2:15][CH2:16][CH2:17][C:18]3[O:22][N:21]=[C:20]([CH3:23])[CH:19]=3)[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[NH3:28]>CO>[CH2:26]([O:25][CH2:24][C:13]1[N:14]([CH2:15][CH2:16][CH2:17][C:18]2[O:22][N:21]=[C:20]([CH3:23])[CH:19]=2)[C:10]2[C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=[C:2]([NH2:28])[C:11]=2[N:12]=1)[CH3:27]Participants
4
Procedure
4-Chloro-2-(ethoxymethyl)-1-[3-(3-methylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinoline (1.87 g, 4.86 mmol) was treated with a solution of 7 M ammonia in methanol (20 mL) according to the procedure described in Part C of Example 5. The crude product was purified by flash chromatography (silica gel, gradient elution from 5% to 20% CMA in chloroform). The appropriate fractions were combined and concentrated to yield a solid that was triturated with 9:1 dichloromethane/methanol. The final material was dried under vacuum to yield 2-(ethoxymethyl)-1-[3-(3-methylisoxazol-5-yl)propyl]-1H-imidazo[4,5-c]quinolin-4-amine (1.29 mg) as a white powder, mp 163.0-164.0° C.
Workup
- customThe crude product was purified by flash chromatography (silica gel, gradient elution from 5% to 20% CMA in chloroform)
- concentrationconcentrated
- customto yield a solid
- customthat was triturated with 9:1 dichloromethane/methanol
- dry with materialThe final material was dried under vacuum
Sources & evidence
- ORD record
- ord-b4359c6905a84004a0d1d11f87916fd1
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915281B2
Reaction notes
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