Hydrochloric Acid → 3-(1-(piperidin-4-yl)-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine

HRID 1775028Notes

Reaction equation

HRID 1775028 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:20]=[CH:19][N:18]([CH:21]5[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]5)[N:17]=4)=[N:14][N:13](C4CCCCO4)[C:10]3=[CH:11][N:12]=2)[CH:2]=1.Cl>O1CCOCC1>[NH:24]1[CH2:23][CH2:22][CH:21]([N:18]2[CH:19]=[CH:20][C:16]([C:15]3[C:9]4[C:10](=[CH:11][N:12]=[C:7]([C:3]5[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=5)[CH:8]=4)[NH:13][N:14]=3)=[N:17]2)[CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71253610tert-butyl 4-(3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Product 1

HCID 712538153-(1-(piperidin-4-yl)-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Tert-butyl 4-(3-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate (17.0 mg, 0.032 mmol) in Dioxane (5 mL) was treated with 4.0 M of Hydrogen chloride in 1,4-Dioxane (5 mL) overnight at room temperature. The reaction mixture was concentrated, and the residue was purified by reverse phase HPLC to afford 215 as an off-white solid (1.2 mg, 18%). 1H NMR (400 MHz, DMSO) δ 9.28 (s, 1H), 9.19 (s, 1H), 8.70-8.57 (m, 2H), 8.44 (d, J=7.6 Hz, 1H), 8.30 (s, 1H), 7.94 (s, 1H), 7.59-7.51 (m, 1H), 6.84 (s, 1H), 4.47 (s, 1H), 3.22 (d, J=12.7 Hz, 2H), 2.82 (t, J=12.0 Hz, 2H), 2.15 (d, J=11.5 Hz, 2H), 2.04 (d, J=9.0 Hz, 2H). ESI MS m/z=346.1 (M+1)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-54915d0b6a384095bc7665c525d19e21
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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