HCID 67520446, compound → 3-[2-Amino-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-3-yl]-isoquinoline-8-carbonitrile trihydrochloride salt

HRID 1926285Notes

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.[C:34]([C:36]1[CH:37]=[CH:38][CH:39]=[C:40]2[C:45]=1[CH:44]=[N:43][C:42](OS(C(F)(F)F)(=O)=O)=[CH:41]2)#[N:35]>>[ClH:4].[ClH:1].[ClH:4].[NH2:33][C:17]1[C:16]([C:42]2[N:43]=[CH:44][C:45]3[C:40]([CH:41]=2)=[CH:39][CH:38]=[CH:37][C:36]=3[C:34]#[N:35])=[CH:21][C:20]([C:22]2[CH:23]=[N:24][N:25]([CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)[CH:26]=2)=[CH:19][N:18]=1

Participants

Reactant 2

HCID 67520446HCID 67520446, compound

HCID 86633148HCID 86633148, compound

Product 1

HCID 675214943-[2-Amino-5-(1-piperidin-4-yl-1h-pyrazol-4-yl)-pyridin-3-yl]-isoquinoline-8-carbonitrile trihydrochloride salt

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 8-cyanoisoquinolin-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=2.30-2.42 (m, 4H), 3.21-3.27 (m, 2H), 3.59 (d, J=13.4 Hz, 2H), 4.59-4.71 (m, 1H), 7.97-8.04 (m, 1H), 8.08 (s, 1H), 8.25-8.30 (m, 2H), 8.42-8.49 (m, 2H), 8.86 (s, 1H), 8.93 (d, J=2.0 Hz, 1H), 9.70 (s, 1H). MS (ES+): m/z=396.19 [MH+]. HPLC: tR=1.67 min (ZQ2, polar—5 min).

Sources & evidence

ORD record: ord-6b89eca1102a4f8faf17c78043a260bb
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178668B2

Reaction notes

Loading…