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

HRID 1775047Notes

Reaction equation

HRID 1775047 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[N:9](COCC[Si](C)(C)C)[N:8]=2)=[N:3]1.Cl>O1CCOCC1>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]2[C:15]3[C:10](=[CH:11][N:12]=[C:13]([C:16]4[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=4)[CH:14]=3)[NH:9][N:8]=2)=[N:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 712536383-(1-methyl-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 712540833-(1-methyl-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridineYield 81%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 3-(1-methyl-1H-pyrazol-3-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine (43.22 mg, 0.1063 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 232 as an off-white solid (23.7 mg, 81%). 1H NMR (400 MHz, DMSO) δ 13.74 (s, 1H), 9.33 (s, 1H), 9.19 (s, 1H), 8.67 (d, J=11.2 Hz, 2H), 8.56 (d, J=7.9 Hz, 1H), 7.85 (s, 1H), 7.63 (s, 1H), 6.82 (s, 1H), 4.01 (s, 3H). ESI MS m/z=277.0 (M+1)

Workup

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

Sources & evidence

ORD record
ord-73b83d041c73470782e36f526820a6d5
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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