Benzenesulfonyl chloride → 5-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide
Reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1)[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.C1(S(Cl)(=O)=O)C=CC=CC=1.[OH-].[NH4+:47]>>[NH2:47][C:9]1[C:8]2[N:17]=[C:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]([CH2:18][CH2:19][CH2:20][CH2:21][C:22]([NH2:24])=[O:23])[C:7]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1Participants
5
Procedure
5-[2-(Ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide (2.25 g, 6.89 mmol) was treated with mCPBA (2.77 g, 12.0 mmol), ammonium hydroxide (40 mL), and benzenesulfonyl chloride (1.71 mL, 13.4 mmol) according to the method described in Part D of Example 36. The crude product was purified by column chromatography on silica gel (eluting with dichloromethane:methanol in a gradient from 90:10 to 85:15). The resulting product was triturated with 10% aqueous sodium hydroxide, isolated by filtration, washed with water, and dried overnight in a vacuum oven to provide 0.752 g of 5-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]pentanamide as a tan solid, mp 198-200° C.
Workup
- customThe crude product was purified by column chromatography on silica gel (
- washeluting with dichloromethane
- customThe resulting product was triturated with 10% aqueous sodium hydroxide
- customisolated by filtration
- washwashed with water
- customdried overnight in a vacuum oven
Sources & evidence
- ORD record
- ord-1fb0899b8c3b4397bcb240056112d596
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697873B2
Reaction notes
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