1-[1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethanone → HCID 178467502, compound

HRID 922464Notes

Reaction equation

HRID 922464 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10]([C:17](=[O:19])[CH3:18])=[N:9]2)=CC=1>FC(F)(F)C(O)=O>[NH:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17](=[O:19])[CH3:18])=[N:9]1

Participants

3

Reactant 1

HCID 580576181-[1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethanone

Product 1

HCID 178467502HCID 178467502, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To 1-[1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethanone (3.14 g) was added trifluoroacetic acid (20 mL), and the mixture was heated to reflux for 2 days. The reaction solution was concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate, and then sequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=95/5→7/3) to give 1-(1H-pyrazolo[3,4-b]pyridin-3-yl)ethanone) [REx(103-1)] (1.73 g) as a pale yellow powder.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 days
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThe resulting residue was diluted with ethyl acetate
  5. washsequentially washed with aqueous saturated sodium hydrogen carbonate solution and saturated saline
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=95/5→7/3)

Sources & evidence

ORD record
ord-e7f04608caca4d2189b9da83e13f3a3e
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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