5-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(7-trifluoromethoxy-isoquinolin-3-yl)-pyridin-2-ylamine trihydrochloride → 3-(6-Fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

HRID 1926282Notes

Reaction equation

HRID 1926282 reaction equation
Cl.Cl.Cl.[NH:4]1[CH2:9][CH2:8][CH:7]([N:10]2[CH:14]=[C:13]([C:15]3[CH:16]=[C:17]([C:22]4[N:23]=[CH:24][C:25]5[C:30]([CH:31]=4)=[CH:29][CH:28]=[C:27](OC(F)(F)F)[CH:26]=5)[C:18]([NH2:21])=[N:19][CH:20]=3)[CH:12]=[N:11]2)[CH2:6][CH2:5]1.[F:37]C1C=C2C(=CC=1)C=NC(OS(C(F)(F)F)(=O)=O)=C2>>[F:37][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[N:23][C:22]([C:17]1[C:18]([NH2:21])=[N:19][CH:20]=[C:15]([C:13]3[CH:12]=[N:11][N:10]([CH:7]4[CH2:6][CH2:5][NH:4][CH2:9][CH2:8]4)[CH:14]=3)[CH:16]=1)=[CH:31]2

Participants

3

Reactant 2

HCID 866331415-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(7-trifluoromethoxy-isoquinolin-3-yl)-pyridin-2-ylamine trihydrochlorideHCID 86633147Trifluoromethanesulfonic acid 6-fluoroisoquinolin-3-yl ester

Product 1

HCID 675213653-(6-Fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine

Procedure

Following the procedure for 5-(1-Piperidin-4-yl-1H-pyrazol-4-yl)-3-(7-trifluoromethoxy-isoquinolin-3-yl)-pyridin-2-ylamine trihydrochloride, using trifluoromethanesulfonic acid 6-fluoroisoquinolin-3-yl ester, the title compound was obtained as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.27-2.39 (m, 4H), 3.18-3.26 (m, 2H), 3.51-3.60 (m, 2H), 4.57-4.70 (m, 1H), 7.79-7.86 (m, 1H), 7.96-8.04 (m, 2H), 8.36 (s, 1H), 8.40 (s, 1H), 8.56 (dd, J=9.2, 5.4 Hz, 1H), 8.70 (s, 1H), 8.74 (s, 1H), 9.77 (s, 1H). MS (ES+): m/z=389.18 [MH+]. HPLC: tR1.68 min (ZQ2, polar—5 min).

Sources & evidence

ORD record
ord-f4d28ac3cc634c8b891557d82ced754c
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

Loading…