4-(2-Methoxyphenyl)thiazole-2-carboxylic acid → N-(5-((6-methoxy-7-(piperidin-4-ylmethoxy)quinolin-4-yl)oxy)pyridin-2-yl)-4-(2-methoxyphenyl)thiazole-2-carboxamide
Reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]4)=[C:16]([O:19][CH3:20])[CH:17]=3)[N:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=1[C:44]1[N:45]=[C:46]([C:49](Cl)=[O:50])[S:47][CH:48]=1.COC1C=CC=CC=1C1N=C(C(O)=O)SC=1>>[CH3:20][O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:21][CH2:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[N:12]=[CH:11][CH:10]=[C:9]2[O:8][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:49]([C:46]2[S:47][CH:48]=[C:44]([C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[O:37][CH3:36])[N:45]=2)=[O:50])=[N:7][CH:6]=1Participants
Reactant 3
Product 1
Procedure
Following the general procedure reported in Preparative Example 16 Step 5 X13 was prepared from tert-butyl 4-(((4-((6-aminopyridin-3-yl)oxy)-6-methoxyquinolin-7-yl)oxy)methyl)piperidine-1-carboxylate and 4-(2-methoxyphenyl)thiazole-2-carbonyl chloride, which was prepared similar to Preparative Example 16 step 4 from commercially available 4-(2-methoxyphenyl)thiazole-2-carboxylic acid. 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.40 (m, 2H), 1.87 (d, J=12.6 Hz, 2H), 2.07 (m, 1H), 2.76 (t, J=11.8 Hz, 2H), 3.18 (d, J=12.6 Hz, 2H), 3.93 (s, 3H), 3.95 (s, 3H), 4.02 (d, J=6.4 Hz, 2H), 6.57 (d, J=5.2 Hz, 1H), 7.09 (t, J=7.6 Hz, 1H), 7.18 (d, J=8.4 Hz, 1H), 7.39 (m, 2H), 7.53 (s, 1H), 7.90 (dd, J=2.8 Hz, J=9.0 Hz, 1H), 8.29 (d, J=9.0 Hz, 1H), 8.49 (m, 4H). MS (ES) C32H31N6O6S requires: 597. Found: 598 (M+H)+.
Workup
- customwas prepared similar
Sources & evidence
- ORD record
- ord-25393c02c5e348719a89fa674946e952
- Source dataset
- uspto-grants-2015_04
- Patent number
- US08999982B2
Reaction notes
Loading…