Trifluoroacetic acid → HCID 178434467, compound

HRID 1629957Notes

Reaction equation

HRID 1629957 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[CH:17]=[C:18]3[C:24]([CH3:25])=[N:23][N:22](CC4C=CC(OC)=CC=4)[C:19]3=[N:20][CH:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([NH:15][C:16]2[CH:17]=[C:18]3[C:24]([CH3:25])=[N:23][NH:22][C:19]3=[N:20][CH:21]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70811059N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine

Product 1

HCID 178434467HCID 178434467, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine (169) (30 mg, 0.063 mmol) in CHCl3 (15 mL) was added trifluoroacetic acid (6 mL) and the reaction mass heated to 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 N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine 170 as a pale yellow colored solid (10 mg). 1H NMR (400 MHz, CDCl3) δ: 8.36 (s, 1H), 7.71 (s, J=2.31, 1H), 6.90 (m, 1H), 6.71 (m, 2H), 5.56 (s, 1H), 3.07 (bs, 4H), 2.62 (bs, 4H), 2.54 (bs, 3H), 2.36 (s, 3H); MS m/z 341.0 (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 N-(3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-amine 170 as a pale yellow colored solid (10 mg)

Sources & evidence

ORD record
ord-c85f4266255346ec9f0b674802d7e33f
Source dataset
uspto-grants-2014_07
Patent number
US08791112B2

Reaction notes

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