Iodoethane → 1-Ethyl-3-{6-[4-(2-trifluoromethylbenzoyl)-piperazin-1-YL]pyridazin-3-YL}-imidazolidin-2-one
Reaction equation
I[CH2:2][CH3:3].[F:4][C:5]([F:33])([F:32])[C:6]1[CH:31]=[CH:30][CH:29]=[CH:28][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[N:20][C:19]([N:22]3[CH2:26][CH2:25][NH:24][C:23]3=[O:27])=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)=[O:9]>>[CH2:2]([N:24]1[CH2:25][CH2:26][N:22]([C:19]2[N:20]=[N:21][C:16]([N:13]3[CH2:12][CH2:11][N:10]([C:8](=[O:9])[C:7]4[CH:28]=[CH:29][CH:30]=[CH:31][C:6]=4[C:5]([F:4])([F:32])[F:33])[CH2:15][CH2:14]3)=[CH:17][CH:18]=2)[C:23]1=[O:27])[CH3:3]Participants
Procedure
Following the procedure as described in Example 2, making variations only as required to use 1-iodoethane in place of 1-iodo-3-methylbutane to react with 1-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl]pyridazin-3-yl}imidazolidin-2-one, the title compound was obtained as a white solid in 72% yield (0.061 g). 1H NMR (300 MHz, CDCl3) δ 8.44 (d, J=9.9 Hz, 1H), 7.72-7.69 (m, 1H), 7.62-7.49 (m, 2H), 7.34-7.32 (m, 1H), 6.99 (d, J=9.9 Hz, 1H), 4.08 (t, J=7.8 Hz, 2H), 3.95-3.84 (m, 2H), 3.6 (t, J=5.1 Hz, 2H), 3.52-3.47 (m, 4H), 3.38-3.25 (m, 4H), 1.16 (t, J=6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ167.4, 156.9, 156.8, 150.03, 134.4, 132.2, 129.3, 127.4, 127.2, 127.02, 126.8, 126.6, 126.2, 125.4, 121.7, 119.9, 118.1, 116.2, 46.4, 45.9, 45.5, 41.2, 41.1, 41.03, 38.3, 12.5. MS (ES+) m/z 449 (M+1).
Sources & evidence
- ORD record
- ord-b3143440b2234e8b8e6b2d9739348205
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767677B2
Reaction notes
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