Isoquinolin-3-yl trifluoromethanesulfonate → 3-Isoquinolin-3-yl-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

HRID 1926261Notes

Reaction equation

[ClH:1].Cl.Cl.[Cl:4][C:5]1[CH:14]=[CH:13][C:12](Cl)=[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.C1C2C(=CC=CC=2)C=C(OS(C(F)(F)F)(=O)=O)N=1>>[ClH:4].[ClH:1].[ClH:4].[CH:10]1[C:11]2[C:6](=[CH:5][CH:14]=[CH:13][CH:12]=2)[CH:7]=[C:8]([C:16]2[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]=2)[N:9]=1

Participants

Reactant 2

HCID 11231236Isoquinolin-3-yl trifluoromethanesulfonate

HCID 67520446HCID 67520446, compound

Product 1

HCID 675208543-Isoquinolin-3-yl-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

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 isoquinolin-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, CD3OD): δ=2.39 (br. s., 4H), 3.22-3.31 (m, 2H), 3.57-3.66 (m, 2H), 4.61-4.74 (m, 1H), 7.95 (t, J=7.5 Hz, 1H), 8.04-8.11 (m, 2H), 8.26 (d, J=8.1 Hz, 1H), 8.33 (s, 1H), 8.38 (d, J=8.3 Hz, 1H), 8.41-8.46 (m, 1H), 8.73 (s, 1H), 8.80-8.86 (m, 1H), 9.64 (s, 1H). MS (ES+): m/z=370.94 [MH+]. HPLC: tR=2.21 min (ZQ2, polar—5 min).

Sources & evidence

ORD record: ord-c2fe211179804a9899ea165310eae510
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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