HCID 178420767, compound → HCID 178420768, compound

HRID 1775017Notes

Reaction equation

HRID 1775017 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[N:8](C3CCCCO3)[N:7]=2)=[N:2]1>Cl.O1CCOCC1>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([C:15]4[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=4)[CH:13]=3)[NH:8][N:7]=2)=[N:2]1

Participants

4

Reactant 1

HCID 178420767HCID 178420767, compound

Product 1

HCID 178420768HCID 178420768, compoundYield 45.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 3-(1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (29.36 mg, 0.08476 mmol) in 4.0 M of Hydrogen chloride in 1,4-Dioxane (5 mL) and 1,4-Dioxane (5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated and the residue was purified by reverse phase HPLC to afford 193 as an off-white solid (10.2 mg, 45.9%). 1H NMR (400 MHz, DMSO) δ 13.71 (s, 1H), 13.14 (s, 1H), 9.23 (d, J=31.1 Hz, 2H), 8.72-8.55 (m, 2H), 8.43 (s, 1H), 7.91 (s, 1H), 7.53 (dd, J=8.0, 4.8 Hz, 1H), 6.84 (s, 1H); ESI MS m/z=263.0 (M+1)

Workup

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

Sources & evidence

ORD record
ord-37947658db1b4202bd874d90d8f0a4dd
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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