HCID 67520446, compound → HCID 67520961, compound

HRID 1926300Notes

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(C=C(OS(C(F)(F)F)(=O)=O)N=C2)=CC=1>>[ClH:4].[ClH:1].[ClH:4].[CH3:34][O:35][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

Reactant 2

HCID 67520446HCID 67520446, compound

HCID 86633154HCID 86633154, compound

Product 1

HCID 67520961HCID 67520961, 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 7-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, CD3OD): δ=2.32-2.44 (m, 4H), 3.23-3.31 (m, 2H), 3.58-3.67 (m, 2H), 4.08 (s, 3H), 4.61-4.72 (m, 1H), 7.67-7.74 (m, 2H), 8.08 (s, 1H), 8.16 (d, J=8.8 Hz, 1H), 8.31 (d, J=2.0 Hz, 1H), 8.40 (s, 1H), 8.65 (s, 1H), 8.79 (d, J=2.0 Hz, 1H), 9.51 (s, 1H). MS (ES+): m/z=401.14 [MH+]. HPLC: tR=1.88 min (ZQ3, polar—5 min).

Sources & evidence

ORD record: ord-d04982d54738415b83534f5300ea45c6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

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