Hydrochloric Acid → 3-(5-Bromo-8-fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

HRID 1926249Notes

Reaction equation

HRID 1926249 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH2:37])=[C:23]([C:25]4[N:26]=[CH:27][C:28]5[C:33]([CH:34]=4)=[C:32]([Br:35])[CH:31]=[CH:30][C:29]=5[F:36])[CH:24]=3)[CH:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:38].CCOCC>C(Cl)Cl>[ClH:38].[ClH:38].[ClH:38].[Br:35][C:32]1[CH:31]=[CH:30][C:29]([F:36])=[C:28]2[C:33]=1[CH:34]=[C:25]([C:23]1[C:22]([NH2:37])=[N:21][CH:20]=[C:19]([C:17]3[CH:16]=[N:15][N:14]([CH:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[CH:18]=3)[CH:24]=1)[N:26]=[CH:27]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 67521074HCID 67521074, compound

Product 1

HCID 675218433-(5-Bromo-8-fluoroisoquinolin-3-yl)-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-pyridin-2-ylamine trihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-{4-[6-amino-5-(5-bromo-8-fluoroisoquinolin-3-yl)-pyridin-3-yl]-pyrazol-1-yl}-piperidine-1-carboxylic acid tert-butyl ester (82 mg, 0.14 mmol) in DCM (3.0 mL) was added 1.0 M of HCl in Et2O (3.0 mL, 3.0 mmol), and the mixture was stirred at ambient temperature for 1 h. Almost immediately a pale yellow solid precipitated. The solvents were evaporated, and the residue was transferred into a vial and dried in vacuo overnight, yielding the title compound as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ=2.09-2.28 (m, 4H), 3.03-3.16 (m, 2H), 3.39 (dd, J=13.8, 1.9 Hz, 2H), 4.47-4.58 (m, 1H), 7.61 (dd, J=9.8, 8.4 Hz, 1H), 8.12 (s, 1H), 8.23-8.32 (m, 2H), 8.42 (s, 1H), 8.46 (s, 1H), 8.48 (d, J=2.0 Hz, 1H), 8.71 (d, J=2.0 Hz, 1H), 9.01 (br. s., 1H), 9.16 (br. s., 1H), 9.65 (s, 1H). MS (ES+): m/z=466.73/468.63 [MH+]. HPLC: tR=1.88 min (ZQ2, polar—5 min).

Workup

  1. customAlmost immediately a pale yellow solid precipitated
  2. customThe solvents were evaporated
  3. customdried in vacuo overnight

Sources & evidence

ORD record
ord-4eca44602273477385643ef744f85d93
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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