Trifluoroacetic acid → HCID 178434466, compound

HRID 715054Notes

Reaction equation

HRID 715054 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([NH:17][C:18]4[CH:23]=[CH:22][C:21]([CH2:24][N:25]5[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]5)=[CH:20][CH:19]=4)[CH:16]=[C:11]3[C:10]([CH3:32])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:32][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[CH:20][CH:19]=3)[CH:16]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 683885461-(4-methoxybenzyl)-3-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-amine

Product 1

HCID 178434466HCID 178434466, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 1-(4-methoxybenzyl)-3-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-amine (166) (40 mg, 0.657 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 8% MeOH/CH2Cl2 obtained pure 3-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-amine 167 as a pale yellow colored solid (10 mg). 1H NMR (400 MHz, CDCl3) δ: 8.38 (s, 1H), 7.76 (s, 1H), 7.52 (s, 1H), 7.21 (d, 1H), 7.19 (d, J=8.41, 1H), 7.19 (s, 1H), 6.89 (d, J=7.92, 1H), 3.46 (s, 2H), 2.54 (m, 8H), 2.31 (s, 3H), 2.05 (s, 3H); MS m/z 336.9 (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 8% MeOH/CH2Cl2 obtained pure 3-methyl-N-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-5-amine 167 as a pale yellow colored solid (10 mg)

Sources & evidence

ORD record
ord-abae3032ccbc418194fba3d3421eacee
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

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