2-(4-(6,7-Dimethoxyquinolin-4-yloxy)phenyl)acetic acid → N-[3-(N-tert-butoxycarbonyl-N-methylamino)-1-(3,4-dimethoxybenzyl)pyrazol-5-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23](O)=[O:24])=[CH:18][CH:17]=1.[NH2:26][C:27]1[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=2)[N:30]=[C:29]([N:43]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH3:44])[CH:28]=1>>[C:48]([O:47][C:45]([N:43]([C:29]1[CH:28]=[C:27]([NH:26][C:23](=[O:24])[CH2:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:21][CH:20]=2)[N:31]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=2)[N:30]=1)[CH3:44])=[O:46])([CH3:51])([CH3:50])[CH3:49]Participants
3
Reactant 2
Product 1
Procedure
Using an analogous procedure to that described in Example 22, 2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetic acid was reacted with 5-amino-3-(N-tert-butoxycarbonyl-N-methylamino)-1-(3,4-dimethoxybenzyl)pyrazole to give N-[3-(N-tert-butoxycarbonyl-N-methylamino)-1-(3,4-dimethoxybenzyl)pyrazol-5-yl]-2-[4-(6,7-dimethoxyquinolin-4-yloxy)phenyl]acetamide as a solid in 66% yield; 1H NMR: (DMSOd6) 1.45 (s, 9H), 3.18 (s, 3H), 3.65 (s, 3H), 3.66 (s, 3H), 3.73 (s, 2H), 3.92 (s, 3H), 3.95 (s, 3H), 5.08 (s, 2H), 6.4 (d, 1H), 6.42 (m, 1H), 6.58 (d, 1H), 6.76 (d, 1H), 6.84 (d, 1H), 7.2 (d, 2H), 7.4 (s, 1H), 7.41 (d, 2H), 7.49 (d, 1H), 10.26 (br s, 1H); Mass Spectrum: M+H+ 684.
Sources & evidence
- ORD record
- ord-82bca64182854110b746f67a50e7e0df
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07973164B2
Reaction notes
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