Piperidin-4-yl-(2-trifluoromethylphenyl)amine → 6-[4-(2-Trifluoromethylphenylamino)piperidin-1-YL]pyridazine-3-carboxylic acid (3-cyclopropylpropyl)amide hydrochloride
Reaction equation
[CH:1]1([CH2:4][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])[CH2:3][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([CH2:4][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])[CH2:3][CH2:2]1Participants
Procedure
Following the procedure as described in Example 1, making variations only as required to use 6-chloropyridazine-3-carboxylic acid (3-cyclopropylpropyl)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 38% yield. m.p. 117-121° C. 1H NMR (300 MHz, DMSO-d6) δ 8.73 (br., s, 1H), 7.90 (d, J=9.3 Hz, 1H), 7.62 (d, J=9.6 Hz, 1H), 7.46-7.37 (m, 2H), 6.99 (d, J=8.4 Hz, 1H), 6.68 (t, J=7.5 Hz, 1H), 4.42 (d, J=13.2 Hz, 2H), 3.82 (br., s, 2H), 3.29-3.22 (m, 3H), 1.98 (d, J=11.7 Hz, 2H), 1.61-1.54 (m, 4H), 1.20-1.13 (m, 2H), 0.65-0.63 (m, 1H), 0.33-0.26 (m, 2H), −0.03-−0.05 (m, 2H). 13C NMR (75 MHz, DMSO-d6) δ 162.1, 157.4, 144.4, 144.1, 133.6, 126.4, 126.3, 116.3, 115.6, 113.0, 112.0, 48.9, 44.4, 31.4, 30.6, 29.2, 10.4, 4.3. MS (ES+) m/z 448.0 (M+1-HCl).
Sources & evidence
- ORD record
- ord-c0d7f7db3f504bb99c4d0afa090e50c8
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951805B2
Reaction notes
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