HCID 67520446, compound → 3-(7-Chloroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

HRID 1926295Notes

Reaction equation

HRID 1926295 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.[Cl:34]C1C=C2C(C=C(OS(C(F)(F)F)(=O)=O)N=C2)=CC=1>>[ClH:4].[ClH:34].[ClH:1].[Cl:34][C:13]1[CH:12]=[C:11]2[C:6]([CH:7]=[C:8]([C:16]3[C:17]([NH2:33])=[N:18][CH:19]=[C:20]([C:22]4[CH:23]=[N:24][N:25]([CH:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)[CH:26]=4)[CH:21]=3)[N:9]=[CH:10]2)=[CH:5][CH:14]=1

Participants

3

Reactant 2

HCID 67520446HCID 67520446, compoundHCID 86633151Trifluoromethanesulfonic acid 7-chloroisoquinolin-3-yl ester

Product 1

HCID 675218193-(7-Chloroisoquinolin-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 7-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, CD3OD): δ=2.29-2.46 (m, 4H), 3.24-3.31 (m, 2H), 3.59-3.67 (m, 2H), 4.61-4.72 (m, 1H), 7.91 (dd, J=8.8, 2.0 Hz 1H), 8.10 (s, 1H), 8.18 (d, J=9.0 Hz, 1H), 8.28 (d, J=2.0 Hz, 1H), 8.30 (d, J=2.0 Hz, 1H), 8.43 (s, 1H), 8.73 (s, 1H), 8.90 (d, J=2.3 Hz, 1H), 9.43 (s, 1H). MS (ES+): m/z=405.09/407.03 [MH+]. HPLC: tR=1.95 min (ZQ3, polar—5 min).

Sources & evidence

ORD record
ord-80808265e7f04840b96efa55bdf33ea7
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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