HCID 67520446, compound → HCID 67520858, compound

HRID 1926302Notes

Reaction equation

HRID 1926302 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.[CH3:34][O:35]C1C=C2C(=CC=1)C=NC(OS(C(F)(F)F)(=O)=O)=C2>>[ClH:4].[ClH:1].[ClH:4].[CH3:34][O:35][C:14]1[CH:5]=[C:6]2[C:11](=[CH:12][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]2

Participants

3

Reactant 2

HCID 67520446HCID 67520446, compoundHCID 86633155HCID 86633155, compound

Product 1

HCID 67520858HCID 67520858, compound

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-methoxyisoquinolin-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=2.16-2.29 (m, 4H), 3.05-3.17 (m, 2H), 3.38 (d, J=12.6 Hz, 2H), 4.00 (s, 3H), 4.48-4.59 (m, 1H), 7.46-7.54 (m, 2H), 8.13 (s, 1H), 8.27 (d, J=8.8 Hz, 1H), 8.48-8.51 (m, 2H), 8.59 (s, 1H), 8.80 (d, J=2.3 Hz, 1H), 9.19 (br. s., 1H), 9.28 (br. s., 1H), 9.45 (s, 1H). MS (ES+): m/z=318.16 [MH+]. HPLC: tR=1.70 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-dbb51e6357de4638b2b08fbaa8780b82
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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