Pentylamine → 6-[4-(5-Fluoro-2-trifluoromethylbenzoyl)piperazin-1-YL]imidazo[1,2-B]pyridazine-2-carboxylic acid pentylamide
Reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].C([O:9][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:38])[C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=4[C:34]([F:37])([F:36])[F:35])[CH2:22][CH2:21]3)=[N:16][N:15]2[CH:39]=1)=O)C>>[CH2:1]([NH:6][C:10]([C:12]1[N:13]=[C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][N:23]([C:26](=[O:38])[C:27]4[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=4[C:34]([F:35])([F:37])[F:36])[CH2:22][CH2:21]3)=[N:16][N:15]2[CH:39]=1)=[O:9])[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Procedure
Following the procedure as described in Example 1, making variations only as required to use n-pentylamine 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 39% yield. 1H NMR (300 MHz, CDCl3) δ 8.16 (s, 1H), 7.76-7.66 (m, 2H), 7.33 (s, 1H), 7.27-7.18 (m, 1H), 7.09-7.03 (m, 1H), 6.89 (d, J=9.9 Hz, 1H), 4.05-3.94 (m, 1H), 3.91-3.8 (m, 1H), 3.69-3.54 (m, 2H), 3.15-3.37 (m, 4H), 3.65-3.29 (m, 2H), 1.67-1.55 (m, 2H), 1.42-1.27 (m, 4H), 0.88 (t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 165.9, 162.6, 162.3, 154.8, 138.3, 136.9, 135.6, 129.7, 129.6, 129.57, 129.5, 126.3, 125.1, 125.4, 122.9, 121.4, 118.3, 116.8, 116.5, 114.9, 114.6, 111.9, 46.2, 45.6, 41.2, 39.2, 29.4, 29.1, 22.4, 14.0. MS (ES+) m/z 507 (M+1).
Sources & evidence
- ORD record
- ord-0bc48af411ff442bb9e45a5b64f3df54
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547698B2
Reaction notes
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