Trifluoroacetic acid → [5-(1-Benzyl-1H-pyrazolo[3,4-b]pyridin-3-yl)furan-2-yl]methanol

HRID 1280438Notes

Reaction equation

HRID 1280438 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[O:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)[CH:3]=1.[Na].O.[CH:23](=O)[CH2:24][CH:25]=O.FC(F)(F)C(O)=O>O1CCOCC1>[CH2:7]([N:6]1[C:2]2=[N:1][CH:23]=[CH:24][CH:25]=[C:3]2[C:4]([C:14]2[O:15][C:16]([CH2:19][OH:20])=[CH:17][CH:18]=2)=[N:5]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15391109HCID 15391109, compoundHCID 86758511HCID 86758511, compound

Product 1

HCID 15391111[5-(1-Benzyl-1H-pyrazolo[3,4-b]pyridin-3-yl)furan-2-yl]methanol

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.69 g (10 mmol) of 5-amino-1-benzyl-3-(5-hydroxymethyl-2-furyl)pyrazole and 1.4 g of malonaldehyde hydrate sodium salt are stirred at 100° C. for 30 min in 100 ml of dioxane and slowly treated with 1.9 ml of trifluoroacetic acid during the course of 5.5 hours. The mixture is evaporated in vacuo, the residue is taken up in ethyl acetate, the mixture is extracted by shaking with K2HPO4 solution, and the organic phase is dried using Na2SO4 and concentrated in vacuo in a rotary evaporator. The residue is chromatographed on silica gel. 200 mg (6.6% of theory) of crystals having a melting point of 104° C. are obtained.

Workup

  1. customThe mixture is evaporated in vacuo
  2. extractionthe mixture is extracted
  3. customthe organic phase is dried
  4. concentrationconcentrated in vacuo in a rotary evaporator
  5. customThe residue is chromatographed on silica gel
  6. customare obtained

Sources & evidence

ORD record
ord-c34350d3ed074aa795282d13163fdc2f
Source dataset
uspto-grants-2002_09
Patent number
US06451805B1

Reaction notes

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