2-Methoxy-4-[2-(4-methylpiperazin-1-yl)ethyl]aniline → HCID 59452679, compound
Reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]3=[N:10][C:9]=2[C:17]2[CH:18]=[CH:19][C:20]([O:34][CH:35]([CH3:37])[CH3:36])=[C:21]([CH:33]=2)[C:22]([NH:24][C:25]2[C:30]([F:31])=[CH:29][CH:28]=[CH:27][C:26]=2[F:32])=[O:23])[CH:5]=[CH:4][N:3]=1.[CH3:38][O:39][C:40]1[CH:46]=[C:45]([CH2:47][CH2:48][N:49]2[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]2)[CH:44]=[CH:43][C:41]=1[NH2:42]>>[F:32][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([F:31])[C:25]=1[NH:24][C:22](=[O:23])[C:21]1[CH:33]=[C:17]([C:9]2[N:10]=[C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]3[C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:42][C:41]3[CH:43]=[CH:44][C:45]([CH2:47][CH2:48][N:49]4[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]4)=[CH:46][C:40]=3[O:39][CH3:38])[N:7]=2)[CH:18]=[CH:19][C:20]=1[O:34][CH:35]([CH3:37])[CH3:36]Participants
Procedure
The title compound (0.092 g, 0.12 mmol, 51%) was prepared from 5-[3-(2-chloro-4-pyrimidinyl)imidazo[1,2-a]pyridin-2-yl]-N-(2,6-difluorophenyl)-2-[(1-methylethyl)oxy]benzamide (Intermediate Example 7) and 2-(methyloxy)-4-[2-(4-methyl-1-piperazinyl)ethyl]aniline (Example 131, step D) in an analogous manner to that described for Example 26, step E. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.39 (d, J=5.9 Hz, 6H), 2.13 (s, 3H), 2.26-2.35 (m, 3H), 2.38-2.45 (m, 3H), 2.52 (d, J=8.8 Hz, 4H), 2.66-2.75 (m, 2H), 3.82 (s, 3H), 4.82-4.91 (m, 1H), 6.63 (d, J=5.1 Hz, 1H), 6.76 (dd, J=8.3, 1.7 Hz, 1H), 6.92-7.03 (m, 2H), 7.19 (t, J=7.9 Hz, 2H), 7.30 (d, J=8.8 Hz, 1H), 7.34-7.40 (m, 1H), 7.44 (dd, J=8.4, 6.2 Hz, 1H), 7.64 (d, J=8.1 Hz, 1H), 7.67-7.77 (m, 2H), 8.07 (d, J=2.2 Hz, 1H), 8.27 (d, J=5.1 Hz, 1H), 8.49 (s, 1H), 9.36 (d, J=6.2 Hz, 1H), 9.70 (s, 1H). MS (M+H, ES+) 733.
Sources & evidence
- ORD record
- ord-4ce221d30eeb4955b14dcfb9a3e2ebad
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08093239B2
Reaction notes
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