Reaction equation
BrC1C=CC2C3N(CC(C)C)C(CCCC)=NC=3C=[N:9]C=2C=1.COC1C=C(OC)C=CC=1B(O)O.[CH2:36]([C:40]1[N:41]([CH2:63][CH:64]([CH3:66])[CH3:65])[C:42]2[C:51]3[CH:50]=[CH:49][C:48]([C:52]4[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][C:53]=4[O:60][CH3:61])=[CH:47][C:46]=3[N:45]=[CH:44][C:43]=2[N:62]=1)[CH2:37][CH2:38][CH3:39]>>[CH2:36]([C:40]1[N:41]([CH2:63][CH:64]([CH3:65])[CH3:66])[C:42]2[C:51]3[CH:50]=[CH:49][C:48]([C:52]4[CH:57]=[CH:56][C:55]([O:58][CH3:59])=[CH:54][C:53]=4[O:60][CH3:61])=[CH:47][C:46]=3[N:45]=[C:44]([NH2:9])[C:43]=2[N:62]=1)[CH2:37][CH2:38][CH3:39]Participants
4
Reactant 3
Product 1
Procedure
7-Bromo-2-butyl-1-isobutyl-1H-imidazo[4,5-c]quinoline and 2,4-dimethoxybenzeneboronic acid were coupled according to the general procedure described in Part J of Example 1. The resulting 2-butyl-7-(2,4-dimethoxyphenyl)-1-isobutyl-1H-imidazo[4,5-c]quinoline was oxidized and then aminated according to the general procedures described in Parts H and I of Example 1 and purified by chromatography on silica gel (8% methanol in CH2Cl2 to 10% methanol in CH2Cl2 gradient) followed by recrystallization from 1/1 ethyl acetate/hexane to afford 2-butyl-7-(2,4-dimethoxyphenyl)-1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine as a pale orange solid, m.p. 187–189° C.
Workup
- custompurified by chromatography on silica gel (8% methanol in CH2Cl2 to 10% methanol in CH2Cl2 gradient)
- customfollowed by recrystallization from 1/1 ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-0657f11f0a2c4022942778090163fb5a
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091214B2
Linked notes
Loading…