5-Fluoro-2-(trifluoromethyl)benzoyl chloride → 6-[4-(5-FLUORO-2-TRIFLUOROMETHYLBENZOYL)PIPERAZIN-1-YL]PYRIDAZINE-3-CARBOXYLIC Acid (4-METHYLPENTYL)AMIDE
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:11]([F:14])([F:13])[F:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:15][CH:16]([CH3:35])[CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:23]1[N:24]=[N:25][C:26]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)=[CH:27][CH:28]=1)=[O:22]>>[CH3:15][CH:16]([CH3:35])[CH2:17][CH2:18][CH2:19][NH:20][C:21]([C:23]1[N:24]=[N:25][C:26]([N:29]2[CH2:34][CH2:33][N:32]([C:7](=[O:8])[C:6]3[CH:10]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[C:11]([F:14])([F:13])[F:12])[CH2:31][CH2:30]2)=[CH:27][CH:28]=1)=[O:22]Participants
3
Procedure
Following the procedure of Example 3, making variations only as required to use 5-fluoro-2-trifluoromethylbenzoyl chloride in place of isoxazole-5-carbonyl chloride to react with 6-piperazin-1-yl-pyridazine-3-carboxylic acid (4-methylpentyl)amide, the title compound was obtained as a white solid (10% yield). 1H NMR (300 MHz, CDCl3) δ 8.04, 7.86, 7.75-7.71, 7.26-7.22, 7.08-7.04, 6.98, 4.10-3.98, 3.90-3.70, 3.46-3.40, 3.36-3.33, 1.61-1.50, 1.28-1.20, 0.85. 13C NMR (75 MHz, CDCl3) 6166.0, 162.9, 162.6, 159.9, 145.5, 136.8, 129.7, 127.6, 127.7, 127.2, 125.1, 123.3, 121.4, 116.8, 116.5, 114.9, 114.6, 113.9, 112.5, 46.3, 44.5, 44.3, 41.3, 39.7, 36.0, 27.8, 27.4, 22.5. MS (ES+) m/z 482.4 (M+1).
Sources & evidence
- ORD record
- ord-d295b56f89ea4a88a86719633be842ab
- Source dataset
- uspto-grants-2008_02
- Patent number
- US07335658B2
Reaction notes
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