1-Bromoheptan-2-one → [4-(2-Pentylimidazo[1,2-B]pyridazin-6-YL)piperazin-1-YL](2-trifluoromethylphenyl)methanone
Reaction equation
Br[CH2:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:10][C:11]1[N:16]=[N:15][C:14]([N:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:19][CH2:18]2)=[CH:13][CH:12]=1>>[CH2:4]([C:3]1[N:10]=[C:11]2[CH:12]=[CH:13][C:14]([N:17]3[CH2:18][CH2:19][N:20]([C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[C:31]([F:34])([F:33])[F:32])=[O:24])[CH2:21][CH2:22]3)=[N:15][N:16]2[CH:2]=1)[CH2:5][CH2:6][CH2:7][CH3:8]Participants
Procedure
Following the procedure as described in Example 2, making variations only as required to 1-bromoheptan-2-one in place of 1-bromobutan-2-one to react with [4-(6-aminopyridazin-3-yl)piperazin-1-yl](2-trifluoromethylphenyl)methanone, the title compound was obtained as a white solid in 62% yield. 1H NMR (300 MHz, CDCl3) δ 7.71-7.69 (m, 1H), 7.64-7.49 (m, 3H), 7.42 (s, 1H), 7.34-7.32 (m, 1H), 6.7 (d, J=9.9 Hz, 1H), 4.01-3.83 (m, 2H), 3.57-3.48 (m, 2H), 3.37-3.27 (m, 4H), 2.73-2.68 (m, 2H), 1.75-1.65 (m, 2H), 1.4-1.25 (m, 4H), 0.91 (t, J=6.9 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 167.5, 154.3, 146.8, 135.7, 134.4, 132.3, 129.4, 127.1, 126.8, 126.7, 126.6, 125.4, 125.3, 121.8, 113.6, 109.3, 46.5, 46.4, 46.2, 41.1, 31.5, 29.1, 29.07, 22.5, 14.0. MS (ES+) m/z 446.2 (M+1).
Sources & evidence
- ORD record
- ord-2aab1947356a4da7ac690db9ff618668
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07547698B2
Reaction notes
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