Piperidin-4-yl-(2-trifluoromethylphenyl)amine → 6-[4-(2-Trifluoromethylphenylamino)piperidin-1-YL]-pyridazine-3-carboxylic acid (2-cyclobutylethyl)amide hydrochloride
Reaction equation
[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1.[NH:17]1[CH2:22][CH2:21][CH:20]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[CH2:19][CH2:18]1>>[ClH:16].[CH:1]1([CH2:5][CH2:6][NH:7][C:8]([C:10]2[N:11]=[N:12][C:13]([N:17]3[CH2:18][CH2:19][CH:20]([NH:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:31])([F:32])[F:33])[CH2:21][CH2:22]3)=[CH:14][CH:15]=2)=[O:9])[CH2:4][CH2:3][CH2:2]1Participants
Procedure
Following the procedure as described in Example 1, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (2-cyclobutylethyl)amide in place of 6-chloropyridazine-3-carboxylic acid (2-cyclopropylethyl)amide to react with piperidin-4-yl-(2-trifluoromethylphenyl)amine, the title compound was obtained as a white powder in 60% yield. 1H NMR (300 MHz, DMSO-d6) δ 8.70 (t, J=5.4 Hz, 1H), 7.91 (d, J=9.6 Hz, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.42-7.36 (m, 2H), 7.00 (d, J=8.4 Hz, 1H), 6.68 (t, J=7.5 Hz, 1H), 4.42 (d, J=13.5 Hz, 2H), 3.81 (s, br., 1H), 3.30-3.13 (m, 4H), 2.29-2.16 (m, 1H), 1.99-1.97 (m, 4H), 1.84-1.55 (m, 8H). 13C NMR (75 MHz, DMSO-d6) δ 162.4, 144.8, 144.6, 134.0, 128.3, 127.2, 126.9, 116.8, 116.1, 113.5, 112.6, 49.3, 44.9, 37.4, 36.6, 33.7, 31.1, 28.2, 18.6. MS (ES+) m/z 448.3 (M+1-HCl).
Sources & evidence
- ORD record
- ord-b5794b3a678948dabb8afab8dd38d018
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951805B2
Reaction notes
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