Methyl iodide → 1-Methyl-3-{6-[4-(2-trifluoromethylbenzoyl)piperazin-1-YL]pyridazin-3-YL}imidazolidin-2-one
Reaction equation
I[CH3:2].[F:3][C:4]([F:32])([F:31])[C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[N:19][C:18]([N:21]3[CH2:25][CH2:24][NH:23][C:22]3=[O:26])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:8]>>[CH3:2][N:23]1[CH2:24][CH2:25][N:21]([C:18]2[N:19]=[N:20][C:15]([N:12]3[CH2:11][CH2:10][N:9]([C:7](=[O:8])[C:6]4[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=4[C:4]([F:3])([F:31])[F:32])[CH2:14][CH2:13]3)=[CH:16][CH:17]=2)[C:22]1=[O:26]Participants
3
Procedure
Following the procedure as described in Example 2, making variations only as required to use 1-iodomethane 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 39% yield (0.020 g). 1H NMR (300 MHz, CDCl3) δ 8.47-8.44 (m, 1H), 7.71 (d, J=7.8 Hz, 1H), 7.62-7.49 (m, 2H), 7.33 (d, J=7.8 Hz, 1H), 7.03-6.99 (m, 1H), 4.08 (t, J=7.8 Hz, 2H), 4.02-3.82 (m, 2H), 3.65-3.42 (m, 6H), 3.31-3.28 (m, 2H), 2.89 (m, 3H). 13C NMR (75 MHz, CD3OD) δ 170.4, 135.4, 133.9, 131.0, 128.8, 127.99, 127.91, 127.85, 47.8, 46.7, 46.6, 45.1, 42.5, 42.4, 31.01, 30.8. MS (ES+) m/z 435 (M+1).
Sources & evidence
- ORD record
- ord-05f50a40a74c4d64828aac8fb3dadb6d
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767677B2
Reaction notes
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