HCID 86602409, compound → HCID 69183122, compound

HRID 2373227Notes

Reaction equation

HRID 2373227 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][O:30][CH3:31])=[C:10]([CH2:19][O:20][CH2:21][C:22]([O:24]C(C)(C)C)=[O:23])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]>FC(F)(F)C(O)=O.C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:29][O:30][CH3:31])=[C:10]([CH2:19][O:20][CH2:21][C:22]([OH:24])=[O:23])[C:11]([C:12]3[CH:13]=[N:14][CH:15]=[C:16]([CH3:18])[CH:17]=3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

3

Reactant 1

HCID 86602409HCID 86602409, compound

Product 1

HCID 69183122HCID 69183122, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

tert-Butyl {[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methoxy}acetate (50 mg) was dissolved in 80% trifluoroacetic acid-DCM (2 ml) and stirred at room temperature for 30 minutes. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel (CHCl3-MeOH 95:5) to give {[1-ethyl-6-(methoxymethyl)-4-(5-methyl-3-pyridyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]methoxy}acetic acid (25 mg) as colorless solid.

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by flash column chromatography on silica gel (CHCl3-MeOH 95:5)

Sources & evidence

ORD record
ord-b8787553c8444db1bc1fe1921911a05f
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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