Hydrochloric Acid → 3-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine trihydrochloride

HRID 1926305Notes

Reaction equation

HRID 1926305 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[C:14]([NH2:31])=[N:15][CH:16]=[C:17]([C:19]3[CH:20]=[N:21][N:22]([CH:24]4[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]4)[CH:23]=3)[CH:18]=1)[N:6]=[CH:7]2.[ClH:32].CCOCC>C(Cl)Cl>[ClH:1].[ClH:32].[ClH:1].[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([F:12])=[C:8]2[C:3]=1[CH:4]=[C:5]([C:13]1[C:14]([NH2:31])=[N:15][CH:16]=[C:17]([C:19]3[CH:20]=[N:21][N:22]([CH:24]4[CH2:25][CH2:26][N:27]([CH3:30])[CH2:28][CH2:29]4)[CH:23]=3)[CH:18]=1)[N:6]=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 44160016HCID 44160016, compound

Product 1

HCID 675215503-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine trihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(5-Chloro-8-fluoroisoquinolin-3-yl)-5-[1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl]-pyridin-2-ylamine (25 mg, 0.057 mmol) in DCM (2.8 mL) was added 1.0 M of HCl in Et2O (2.8 mL, 2.8 mmol), causing a solid to precipitate. The solid was filtered off, washed with DCM and heptane, and dried in vacuo, yielding the title compound as yellow solid. 1H NMR (400 MHz, CD3OD): δ=2.36-2.47 (m, 4H), 3.67-3.76 (m, 2H), 4.19-4.24 (m, 1H), 4.58-4.69 (m, 1H), 4.70 (s, 1H), 7.47-7.54 (m, 1H), 8.00 (dd, J=8.3, 4.8 Hz, 1H), 8.05-8.09 (m, 1H), 8.29 (s, 1H), 8.38 (s, 1H), 8.71 (s, 1H), 8.83 (s, 1H), 9.68 (s, 1H).

Workup

  1. customto precipitate
  2. filtrationThe solid was filtered off
  3. washwashed with DCM and heptane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8a43e022e73b4bd28607efa2aab438ac
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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