4-Fluorobenzylamine → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid 4-fluorobenzylamide
Reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[CH:4][CH:3]=1.C([O:12][C:13]([C:15]1[N:16]=[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][N:26]([C:29](=[O:41])[C:30]4[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=4[C:37]([F:40])([F:39])[F:38])[CH2:25][CH2:24]3)=[N:19][N:18]2[CH:42]=1)=O)C>>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:7][C:13]([C:15]2[N:16]=[C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][N:26]([C:29](=[O:41])[C:30]5[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=5[C:37]([F:38])([F:40])[F:39])[CH2:25][CH2:24]4)=[N:19][N:18]3[CH:42]=2)=[O:12])=[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 4-fluorobenzylamine 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 38% yield. 1H NMR (300 MHz, CDCl3) δ 8.19 (d, J=3.0 Hz, 1H), 7.76-7.72 (m, 1H), 7.69-7.6 (m, 2H), 7.35-7.3 (m, 2H), 7.27-7.19 (m, 1H), 7.09-6.94 (m, 3H), 6.89 (d, J=9.9 Hz, 1H), 4.59 (d, J=6.3 Hz, 2H), 4.05-3.94 (m, 1H), 3.91-3.8 (m, 1H), 3.69-3.54 (m, 2H), 3.52-3.43 (m, 2H), 3.38-3.29 (m, 2H). 13C NMR (75 MHz, CDCl3) δ 166.0, 162.6, 162.1, 160.5, 154.8, 137.6, 135.5, 134.1, 134.0, 129.7, 129.6, 126.2, 118.6, 116.8, 116.6, 115.6, 115.3, 114.9, 114.6, 112.2, 46.2, 45.6, 42.5, 41.3. MS (ES+) m/z 508 (M+1).
Sources & evidence
- ORD record
- ord-5c9e5ae7bf3a4b5ebafe4a327b03e646
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547698B2
Reaction notes
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