Trifluoroacetic acid → HCID 66555776, compound

HRID 1629928Notes

Reaction equation

HRID 1629928 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[CH:16]=[C:11]3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:22][N:20]1[CH:21]=[C:17]([C:15]2[CH:16]=[C:11]3[CH:10]=[N:9][NH:8][C:12]3=[N:13][CH:14]=2)[CH:18]=[N:19]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388453HCID 68388453, compound

Product 1

HCID 66555776HCID 66555776, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-methoxybenzyl)-5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridine (116) (40 mg, 0.125 mmol) dissolved in chloroform (10 mL) was added trifluoroacetic acid (5 mL) and the reaction mixture was heated at 50° C. for 12 h. After completion of the reaction the solvents were removed and diluted with cold water, pH was adjusted to 8 and the aqueous phase extracted with chloroform two times. The organic layer was washed with brine solution and dried over sodium sulphate and the solvents were removed. The crude was passed through 100-200 mesh silica gel eluting the compound at 40% ethyl acetate in hexane as pale yellow solid of 5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrazolo[3,4-b]pyridine 117 obtained in 10 mg quantity. MS m/z 199.9 (M+H)+.

Workup

  1. customAfter completion of the reaction the solvents
  2. customwere removed
  3. additiondiluted with cold water, pH
  4. extractionthe aqueous phase extracted with chloroform two times
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvents were removed
  8. customobtained in 10 mg quantity

Sources & evidence

ORD record
ord-e841f34b6cf6494c85278b0fe365c9e6
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

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