Trifluoroacetic acid → HCID 66732718, compound

HRID 1966832Notes

Reaction equation

HRID 1966832 reaction equation
COC1C=CC(C[N:8]2[C:12]3[N:13]=[CH:14][C:15]([C:24]4[CH2:31][C:27]5([CH2:30][CH2:29][CH2:28]5)[O:26][N:25]=4)=[C:16]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)[C:11]=3[CH:10]=[N:9]2)=CC=1.FC(F)(F)C(O)=O>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH2:28]1[C:27]2([CH2:31][C:24]([C:15]3[CH:14]=[N:13][C:12]4[NH:8][N:9]=[CH:10][C:11]=4[C:16]=3[NH:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)=[N:25][O:26]2)[CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66732413HCID 66732413, compound

Product 1

HCID 66732718HCID 66732718, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

1-(4-Methoxybenzyl)-5-(5-oxa-6-azaspiro[3.4]oct-6-en-7-yl)-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.8 gm, 4 mmol) (example 9) was dissolved in trifluoroacetic acid (4.56 gm, 40 mmol) and the reaction mixture was stirred for about 4 hours at room temperature under nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate and sodium bicarbonate solution was added drop wise. It was extracted with ethyl acetate, organic layer was washed with water, brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The crude product was purified by column chromatography.

Workup

  1. additionwas added drop wise
  2. extractionIt was extracted with ethyl acetate, organic layer
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cff19ef678ce4360afb3efaa0e25ac60
Source dataset
uspto-grants-2013_04
Patent number
US08420666B2

Reaction notes

Loading…