HCID 178451761, compound → HCID 178509399, compound

HRID 489436Notes

Reaction equation

HRID 489436 reaction equation
[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]3[C:15]([C:16]#[N:17])=[C:14]([CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)[NH:13][C:12]4=[N:31][NH:32][CH:33]=[C:11]34)=[CH:8][CH:7]=[CH:6][C:5]=12>FC(F)(F)C(O)=O>[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]3[C:15]([C:16]#[N:17])=[C:14]([CH:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]4)[NH:13][C:12]4=[N:31][NH:32][CH:33]=[C:11]34)=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

3

Reactant 1

HCID 178451761HCID 178451761, compound

Product 1

HCID 178509399HCID 178509399, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(2,1,3-Benzoxadiazol-4-yl)-6-(1-t-butoxycarbonylpiperidin-4-yl)-5-cyano-4,7-dihydro-2H-pyrazolo[3,4-b]pyridine (1.7 g) was added to trifluoroacetic acid (20 mL) at 0° C. and the mixture was stirred for an hour. The solvent was evaporated under reduced pressure. After alkalification with sodium bicarbonate, the mixture was extracted with ethyl acetate. The solvent was evaporated under reduced pressure and the residue was washed with acetonitrile, and the precipitated crystals were collected by filtration to give the title compound (0.83 g) as yellow crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionAfter alkalification with sodium bicarbonate, the mixture was extracted with ethyl acetate
  3. customThe solvent was evaporated under reduced pressure
  4. washthe residue was washed with acetonitrile
  5. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-ff1337bb489346309be118eafca7749d
Source dataset
uspto-grants-2005_12
Patent number
US06977262B2

Reaction notes

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