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

HRID 1926287Notes

Reaction equation

HRID 1926287 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:45]=[CH:44][C:43]([F:46])=[C:42]2[C:37]=1[CH:38]=[C:39](OS(C(F)(F)F)(=O)=O)[N:40]=[CH:41]2)#[N:35]>>[ClH:4].[ClH:1].[ClH:4].[NH2:33][C:17]1[C:16]([C:39]2[N:40]=[CH:41][C:42]3[C:43]([F:46])=[CH:44][CH:45]=[C:36]([C:34]#[N:35])[C:37]=3[CH:38]=2)=[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

3

Reactant 2

HCID 67520446HCID 67520446, compoundHCID 86633149Trifluoromethanesulfonic acid 5-cyano-8-fluoroisoquinolin-3-yl ester

Product 1

HCID 675206173-[2-Amino-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-3-yl]-8-fluoro-isoquinoline-5-carbonitrile 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-cyano-8-fluoroisoquinolin-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=2.26-2.42 (m, 4H), 3.20-3.29 (m, 2H), 3.55-3.63 (m, 2H), 4.55-4.67 (m, 1H), 7.54 (dd, J=9.7, 8.2 Hz, 1H), 7.95 (s, 1H), 8.15 (s, 1H), 8.26 (d, J=2.0 Hz, 1H), 8.30 (d, J=2.3 Hz, 1H), 8.35 (dd, J=8.1, 5.1 Hz, 1H), 8.39 (s, 1H), 9.70 (d, J=1.0 Hz, 1H). MS (ES+): m/z=414.13 [MH+]. HPLC: tR=1.70 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-27b169f9f2a649a7ada7c333404b4efd
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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