2-(Trifluoromethyl)benzoyl chloride → [4-(6-Phenylpyridazin-3-YL)piperazin-1-YL]-(2-trifluoromethylphenyl)methanone
Reaction equation
[C:1]1([C:7]2[N:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24]>>[C:1]1([C:7]2[N:8]=[N:9][C:10]([N:13]3[CH2:18][CH2:17][N:16]([C:23]([C:22]4[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=4[C:20]([F:19])([F:30])[F:31])=[O:24])[CH2:15][CH2:14]3)=[CH:11][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
3
Procedure
Following the procedure as described in Example 5, making variations only as required to use 3-phenyl-6-piperazin-1-ylpyridazine in place of 3-piperazin-1-yl-6-pyridin-2-ylpyridazine to react with 2-trifluoromethylbenzoyl chloride, the title compound was obtained as an off-white solid in 67% yield (0.312 g). 1H NMR (300 MHz, CDCl3) δ 7.97-7.95 (m, 2H), 7.73-7.71 (m, 2H), 7.63-7.51 (m, 2H), 7.47-7.39 (m, 3H), 7.34 (d, J=7.3 Hz, 1H), 7.06 (d, J=9.9 Hz, 1H), 4.10-3.67 (m, 6H), 3.35-3.32 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 167.6, 158.2, 151.7, 135.9, 134.3, 132.4, 129.5, 129.2, 128.9, 127.3, 126.9, 126.1, 114.2, 46.5, 45.2, 44.9, 41.3. MS (ES+) m/z 413.0 (M+1).
Sources & evidence
- ORD record
- ord-cf5f2b3eb303459dbd9bd8b2e1b27ed4
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07767677B2
Reaction notes
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