Trifluoroacetic acid → HCID 178460022, compound

HRID 715048Notes

Reaction equation

HRID 715048 reaction equation
COC1C=CC(C[N:8]2[C:12]3=[N:13][CH:14]=[C:15]([C:17]4[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=4)[CH:16]=[C:11]3[C:10]([CH3:28])=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[CH3:28][C:10]1[C:11]2[C:12](=[N:13][CH:14]=[C:15]([C:17]3[CH:18]=[C:19]([NH:23][C:24](=[O:27])[CH:25]=[CH2:26])[CH:20]=[CH:21][CH:22]=3)[CH:16]=2)[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68388524N-(3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acrylamide

Product 1

HCID 178460022HCID 178460022, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-(3-(1-(4-methoxybenzyl)-3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acrylamide (154) (70 mg) in CHCl3 (20 mL) was added trifluoroacetic acid (5 mL) and the reaction mixture heated at 50° C. for 12. After completion of the reaction the solvents were removed, diluted with cold water, pH was adjusted to 8 and the aqueous phase extracted with chloroform twice. The organic layer was washed with brine solution and dried over sodium sulphate and the solvent completely distilled off to get the crude product. The crude was passed through 100-200 mesh silica gel, eluting the pure compound in 60% EtOAc/hexane gave pale yellow solid compound N-(3-(3-methyl-1H-pyrazolo[3,4-b]pyridin-5-yl)phenyl)acrylamide 155. 1H NMR (400 MHz, CDCl3) δ: 10.29 (s, H), 8.75 (d, J=2.07, 1H), 8.40 (d, J=1.95, 1H), 8.03 (s, 1H), 7.69 (s, 1H), 7.43 (m, 1H), 6.50 (m, 1H), 6.46 (m, 1H), 6.26 (m, 1H), 2.55 (bs, 3H); MS m/z 277.9 (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 twice
  5. washThe organic layer was washed with brine solution
  6. dry with materialdried over sodium sulphate
  7. distillationthe solvent completely distilled off
  8. customto get the crude product
  9. washeluting the pure compound in 60% EtOAc/hexane

Sources & evidence

ORD record
ord-81d9194f4147433fb93bce60e204e425
Source dataset
uspto-grants-2015_11
Patent number
US09187473B2

Reaction notes

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