p-Fluorophenethylamine → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid [2-(4-fluoro-phenyl)ethyl]amide
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[CH:4][CH:3]=1.C([O:13][C:14]([C:16]1[N:17]=[C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][N:27]([C:30](=[O:42])[C:31]4[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=4[C:38]([F:41])([F:40])[F:39])[CH2:26][CH2:25]3)=[N:20][N:19]2[CH:43]=1)=O)C>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:14]([C:16]2[N:17]=[C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][N:27]([C:30](=[O:42])[C:31]5[CH:36]=[C:35]([F:37])[CH:34]=[CH:33][C:32]=5[C:38]([F:39])([F:41])[F:40])[CH2:26][CH2:25]4)=[N:20][N:19]3[CH:43]=2)=[O:13])=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Procedure
Following the procedure as described in Example 1, making variations only as required to use 2-(4-fluorophenyl)ethylamine in place of isoamylamine to react with 6-[4-(5-fluoro-2-trifluoromethylbenzoyl)piperazin-1-yl]imidazo[1,2-b]pyridazine-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid in 42% yield. 1H NMR (300 MHz, CDCl3) δ 8.15 (d, J=3.0 Hz, 1H), 7.76-7.7 (m, 1H), 7.65 (d, J=9.9 Hz, 1H), 7.33 (t, J=6.0 Hz, 1H), 7.27-7.12 (m, 3H), 7.09-7.02 (m, 1H), 7.0-6.91 (m, 2H), 6.87 (d, J=9.9 Hz, 1H), 4.04-3.92 (m, 1H), 3.91-3.79 (m, 1H), 3.71-3.53 (m, 4H), 3.51-3.4 (m, 2H), 3.36-3.28 (m, 2H), 2.88 (t, J=7.2 Hz, 2H). 13C NMR (75 MHz, CDCl3) δ 165.9, 163.2, 162.4, 160.0, 154.8, 138.1, 135.6, 134.6, 134.58, 130.3, 130.1, 129.7, 129.6, 129.57, 129.5, 126.4, 118.3, 116.8, 116.5, 115.5, 115.2, 114.9, 114.6, 111.9, 46.2, 45.6, 41.3, 40.5, 35.2. MS (ES+) m/z 559 (M+1).
Sources & evidence
- ORD record
- ord-6a0e1dd3589b4595a2e9fe58bda4b64f
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547698B2
Reaction notes
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