6-Chloropyridazine-3-carboxylic acid pentylamide → HCID 86617126, compound
Reaction equation
[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)=[O:8])[CH2:2][CH2:3][CH2:4][CH3:5].[NH:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]([F:32])([F:31])[F:30])[CH2:18][CH2:17]1>>[ClH:15].[CH2:1]([NH:6][C:7]([C:9]1[N:10]=[N:11][C:12]([N:16]2[CH2:17][CH2:18][CH:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[C:29]([F:30])([F:31])[F:32])[CH2:20][CH2:21]2)=[CH:13][CH:14]=1)=[O:8])[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 6-chloropyridazine-3-carboxylic acid pentylamide 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 37% yield. 1H NMR (300 MHz, DMSO-d6) δ 8.79 (t, J=5.4 Hz, 1H), 7.94 (d, J=9.9 Hz, 1H), 7.66 (d, J=9.6 Hz, 1H), 7.50-7.40 (m, 2H), 7.05-7.02 (m, 1H), 6.72 (t, J=7.5 Hz, 1H), 4.48 (d, J=13.2 Hz, 2H), 3.83 (br., s, 1H), 3.34-3.26 (m, 4H), 2.02 (d, J=10.8 Hz, 2H), 1.65-1.50 (m, 4H), 1.37-1.16 (m, 4H), 0.86 (t, J=6.3 Hz, 3H). 13C NMR (75 MHz, DMSO-d6) δ 162.0, 157.3, 144.4, 144.1, 133.6, 127.9, 126.8, 126.5, 123.2, 116.5, 115.7, 113.0, 112.2, 48.9, 44.5, 30.6, 28.8, 28.6, 21.8, 13.9. MS (ES+) m/z 436.2 (M+1-HCl).
Sources & evidence
- ORD record
- ord-3b5cdbc02a994944bc693d0e283b6d36
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07951805B2
Reaction notes
Loading…