1-Heptanamine → 5-[4-(2-Trifluoromethylbenzoyl)piperazin-1-YL]-[1,3,4]thiadiazole-2-carboxylic acid heptylamide
Reaction equation
[CH2:1]([NH2:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].C([O:11][C:12]([C:14]1[S:15][C:16]([N:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:36])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH2:21][CH2:20]2)=[N:17][N:18]=1)=O)C>>[CH2:1]([NH:8][C:12]([C:14]1[S:15][C:16]([N:19]2[CH2:20][CH2:21][N:22]([C:25](=[O:36])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]([F:35])([F:34])[F:33])[CH2:23][CH2:24]2)=[N:17][N:18]=1)=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]Participants
Procedure
Following the procedure as described in Example 3, making variations only as required to use n-heptylamine in place of isoamylamine to react with 5-[4-(2-trifluoromethylbenzoyl)piperazin-1-yl][1,3,4]thiadiazole-2-carboxylic acid ethyl ester, the title compound was obtained as a white solid (0.053 g, yield 90%). 1H NMR (300 MHz, CDCl3) δ 7.69-7.76 (m, 1H), 7.63-7.50 (m, 2H), 7.30-7.38 (m, 1H), 7.05 (br. t, 1H), 4.07-4.01 (m, 1H), 3.91-3.83 (m, 1H), 3.75-3.6 (m, 2H), 3.54-3.5 (m, 2H), 3.43-3.31 (m, 4H), 1.59-1.52 (m, 2H), 1.32-1.21 (m, 8H), 0.85 (t, J=6.6 Hz, 3H). 13C NMR (75 MHz, CDCl3) δ 174.5, 167.5, 158.2, 156.0, 133.9, 133.9, 132.4, 129.6, 127.1, 126.9, 126.8, 125.3, 121.7, 49.5, 48.9, 45.9, 40.7, 39.6, 31.6, 29.4, 28.8, 26.7, 22.5, 14.0. MS (ES+) m/z 484 (M+1).
Sources & evidence
- ORD record
- ord-5c455a814a8742c9835968263ded29e0
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07919496B2
Reaction notes
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