3-(5,8-dichloroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride → 3-(6-Chloroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride
Reaktionsgleichung
[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(=CC=1)C=NC(OS(C(F)(F)F)(=O)=O)=C2>>[ClH:4].[ClH:34].[ClH:1].[Cl:15][C:12]1[CH:11]=[C:6]2[C:5](=[CH:14][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[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)[CH:26]=3)[CH:21]=1)=[CH:7]2Komponenten
3
Edukt 2
Produkt 1
Versuchsvorschrift
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-chloroisoquinolin-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=2.14-2.31 (m, 4H), 3.04-3.16 (m, 2H), 3.33-3.41 (m, 2H), 4.47-4.62 (m, 3H), 7.83 (dd, J=8.8, 2.0 Hz, 1H), 8.15 (s, 1H), 8.21 (d, J=1.8 Hz, 1H), 8.34 (d, J=8.8 Hz, 1H), 8.50 (d, J=2.0 Hz, 1H), 8.54 (s, 1H), 8.73 (s, 1H), 8.84 (d, J=2.0 Hz, 1H), 9.22 (br. s., 1H), 9.34 (br. s., 1H), 9.52 (s, 1H), MS(ES+): m/z=404.90/406.78 [MH+]. HPLC: tR=1.80 min (ZQ2, polar—5 min).