HCID 67520446, compound → 3-(5,8-Difluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

HRID 1926256Notes

Reaction equation

HRID 1926256 reaction equation
[ClH:1].Cl.Cl.[Cl:4]C1C=CC(Cl)=C2C=1C=C([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=C2.[F:34][C:35]1[CH:44]=[CH:43][C:42]([F:45])=[C:41]2[C:36]=1[CH:37]=[C:38](OS(C(F)(F)F)(=O)=O)[N:39]=[CH:40]2>>[ClH:4].[ClH:1].[ClH:4].[F:34][C:35]1[CH:44]=[CH:43][C:42]([F:45])=[C:41]2[C:36]=1[CH:37]=[C:38]([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)[N:39]=[CH:40]2

Participants

3

Reactant 2

HCID 67520446HCID 67520446, compoundHCID 86633139Trifluoromethanesulfonic acid 5,8-difluoroisoquinolin-3-yl ester

Product 1

HCID 675213283-(5,8-Difluoroisoquinolin-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 5,8-difluoroisoquinolin-3-yl ester in place of trifluoromethanesulfonic acid 5,8-dichloroisoquinolin-3-yl ester, affording the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.09-2.30 (m, 4H), 3.04-3.17 (m, 2H), 3.41 (d, J=12.1 Hz, 2H), 4.48-4.59 (m, 1H), 7.57-7.68 (m, 1H), 7.79 (td, J=8.8, 3.6 Hz, 1H), 8.15 (s, 1H), 8.47 (s, 1H), 8.68 (s, 1H), 8.83 (br. s., 1H), 9.01 (br. s., 1H), 9.65 (s, 1H). MS (ES+): m/z=407.16 [MH+]. HPLC: tR=1.76 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-aa5dfa5f4f354b8cb3c30be5f560924e
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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