3-Methoxypropanoyl chloride → 1-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([N+:12]([O-])=O)=[C:5]2[NH:15][CH2:16][CH2:17][CH2:18][N:19]1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24].[CH3:25][O:26][CH2:27][CH2:28][C:29](Cl)=O>>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:29]([CH2:28][CH2:27][O:26][CH3:25])[N:15]([CH2:16][CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])[C:5]=3[C:4]=2[CH:3]=1Participants
3
Procedure
1-[3-(6-Bromo3-nitroquinolin-4-ylamino)propyl]pyrrolidin-2-one was treated according to the methods described in Parts B, C, and D of Examples 152-156. 3-Methoxypropionyl chloride was used in Part C. The crude product obtained in Part D was recrystallized from acetonitrile. The crystals were washed with cold acetonitrile and diethyl ether and dried in a vacuum oven at 60° C. to provide 1-{3-[8-bromo-2-(2-methoxyethyl)-1H-imidazo[4,5-c]quinolin-1-yl]propyl}pyrrolidin-2-one as a light grey solid.
Workup
- customThe crude product obtained in Part D
- customwas recrystallized from acetonitrile
- washThe crystals were washed with cold acetonitrile and diethyl ether
- customdried in a vacuum oven at 60° C.
Sources & evidence
- ORD record
- ord-e2eed0579ca34221a8ac51a2f3131d44
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598382B2
Reaction notes
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