Trifluoroacetic acid → HCID 178468820, compound

HRID 1629929Notes

Reaction equation

HRID 1629929 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20]([O-:22])=[O:21])[CH:16]=[C:11]3[C:10]([CH3:26])=[N:9]2)=CC=1.F[C:30](F)(F)[C:31](O)=O>C(Cl)(Cl)Cl>[CH3:26][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([O:22][CH2:30][CH3:31])=[O:21])[CH:16]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86681766HCID 86681766, compound

Product 1

HCID 178468820HCID 178468820, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate (118) (70 mg, 0.74 mmol) dissolved in chloroform (5 mL) was added trifluoroacetic acid (8 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 ethyl 3-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)benzoate 119 obtained in 10 mg quantity. MS m/z 281.9 (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-7d237326844848d3b6d8b33a15c55946
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

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