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) δ 166.0, 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-51a1fcafa6054e32b0ce1b7ecac9fda8
- Source dataset
- uspto-grants-2011_06
- Patent number
- US07964591B2
Reaction notes
Loading…