2-(Chloromethyl)-4-fluoro-1-(trifluoromethyl)benzene → 6-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (3-METHYLBUTYL)AMIDE
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[C:6]([CH:9]=1)[CH2:7]Cl.[CH3:14][CH:15]([CH3:33])[CH2:16][CH2:17][NH:18][C:19]([C:21]1[N:22]=[N:23][C:24]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:25][CH:26]=1)=[O:20]>>[CH3:14][CH:15]([CH3:33])[CH2:16][CH2:17][NH:18][C:19]([C:21]1[N:22]=[N:23][C:24]([N:27]2[CH2:32][CH2:31][N:30]([CH2:7][C:6]3[CH:9]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[C:10]([F:13])([F:12])[F:11])[CH2:29][CH2:28]2)=[CH:25][CH:26]=1)=[O:20]Participants
3
Procedure
Following the procedure of Example 11, making variations only as required to use 5-fluoro-2-trifluoromethylbenzyl chloride in place of 2-trifluoromethylbenzyl chloride to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (3-methylbutyl)amide, the title compound was obtained as a white solid (34% yield). 1H NMR (300 MHz, CDCl3) δ 8.02, 7.82-7.92, 7.57-7.68, 7.00-7.09, 6.96, 3.79, 3.71, 3.50, 2.64, 1.64-1.78, 1.51, 0.94. MS (ES+) m/z 454 (M+1).
Sources & evidence
- ORD record
- ord-996c9f1e2ba74f5c9f20f9e53e8f3406
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335658B2
Reaction notes
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