Trifluoroacetic acid → HCID 178434465, compound

HRID 1629953Notes

Reaction equation

HRID 1629953 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([NH:17][C:18]4[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=4)[CH2:21][N:22]4[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][OH:30])[CH2:24][CH2:23]4)[CH:16]=[C:11]3[C:10]([CH3:34])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:34][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([NH:17][C:18]3[CH:19]=[C:20]([CH:31]=[CH:32][CH:33]=3)[CH2:21][N:22]3[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][OH:30])[CH2:26][CH2:27]3)[CH:16]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388571HCID 68388571, compound

Product 1

HCID 178434465HCID 178434465, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2-(4-(3-((1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)amino)benzyl)piperazin-1-yl)ethanol (163) (50 mg, 0.103 mmol) in CHCl3 (10 mL) was added trifluoroacetic acid (6 mL) and the reaction mass heated at 60° C. overnight. After completion of the reaction the solvents were completely distilled off and diluted with water and the pH was adjusted to 9 and extracted with chloroform twice. The combined organic layer was washed with brine solution and dried over sodium sulphate and the solvents were removed and the crude material was passed through 100-200 mesh silica gel, eluting with 10% MeOH/CH2Cl2 obtained pure 2-(4-(3-((3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)amino)benzyl)piperazin-1-yl)ethanol 164 as a pale yellow colored solid (6 mg). MS m/z 353.54 (M+H)+.

Workup

  1. customAfter completion of the reaction the solvents
  2. distillationwere completely distilled off
  3. additiondiluted with water
  4. extractionextracted with chloroform twice
  5. washThe combined organic layer was washed with brine solution
  6. dry with materialdried over sodium sulphate
  7. customthe solvents were removed
  8. washeluting with 10% MeOH/CH2Cl2 obtained pure 2-(4-(3-((3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)amino)benzyl)piperazin-1-yl)ethanol 164 as a pale yellow colored solid (6 mg)

Sources & evidence

ORD record
ord-73ce97b378044e89aabc27b489e41c3e
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

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