HCID 67520446, compound → 3-(6,8-Dichloroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride
Reaction equation
[ClH:1].Cl.Cl.[Cl:4][C:5]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:6]=1[CH:7]=[C:8]([C:16]1[C:17]([NH2:33])=[N:18][CH:19]=[C:20]([C:22]3[CH:23]=[N:24][N:25]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH:26]=3)[CH:21]=1)[N:9]=[CH:10]2.[Cl:34]C1C=C2C(=C(Cl)C=1)C=NC(OS(C(F)(F)F)(=O)=O)=C2>>[ClH:4].[ClH:34].[ClH:1].[Cl:34][C:14]1[CH:5]=[C:6]2[C:11](=[C:12]([Cl:15])[CH:13]=1)[CH:10]=[N:9][C:8]([C:16]1[C:17]([NH2:33])=[N:18][CH:19]=[C:20]([C:22]3[CH:23]=[N:24][N:25]([CH:27]4[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]4)[CH:26]=3)[CH:21]=1)=[CH:7]2Participants
Procedure
The procedure for the preparation of 3-(5,8-dichloroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride was followed, except using trifluoromethanesulfonic acid 6,8-dichloroisoquinolin-3-yl ester in place of trifluoromethanesulfonic acid 5,8-dichloroisoquinolin-3-yl ester. This afforded the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.10-2.31 (m, 4H), 3.04-3.18 (m, 2H), 3.33-3.46 (m, 2H), 4.45-4.59 (m, 1H). 8.11 (d, J=1.8 Hz, 1H), 8.14 (s, 1H), 8.22 (d, J=1.3 Hz, 1H), 8.48 (d, J=2.0 Hz, 1H), 8.50 (s, 1H), 8.63 (br. s., 1H), 8.75 (s, 1H), 8.83 (d, J=2.0 Hz, 1H), 8.95 (br. s., 1H), 9.07 (br. s., 1H), 9.65 (s, 1H). MS (ES+): m/z=439.07/441.07/443.06 [MH+]. HPLC: tR=2.00 min (ZQ2, polar—5 min).
Sources & evidence
- ORD record
- ord-6c19f4e420b74fb4a2ff3f625ff60d64
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178668B2
Reaction notes
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