HCID 57717544, compound → HCID 57717532, compound

HRID 1984533Notes

Reaction equation

HRID 1984533 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[C:14](=[N:20][N:21]([CH2:23][CH3:24])[CH:22]=3)[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1>C(O)C.CO.[Pd].CN(C=O)C>[NH2:19][C:15]1[C:14]2=[N:20][N:21]([CH2:23][CH3:24])[CH:22]=[C:13]2[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:18][C:17]=2[N:16]=1

Participants

6

Reactant 1

HCID 57717544HCID 57717544, compound

Product 1

HCID 57717532HCID 57717532, compoundYield 54.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 7-benzyloxy-2-ethyl-2H-pyrazolo[3,4-c]quinolin-4-ylamine (prepared as described in Example 1320) (0.80 g, 2.51 mmol) in ethanol (80 mL) and methanol (20 mL) and palladium on carbon (10% palladium w/w on carbon) (0.4 g, ) were combined in a pressure vessel and placed under hydrogen pressure ((50 psi (3.4×105 Pa)) for 24 hours. The reaction mixture was diluted with DMF (50 mL), filtered through CELITE filter agent, and the filtrate was concentrated under reduced pressure. The residue was purified via column chromatography on silica gel (eluting with 20-50% CMA/chloroform), concentrated under reduced pressure, and crystallized from acetonitrile to yield 0.31 g of 4-amino-2-ethyl-2H-pyrazolo[3,4-c]quinolin-7-ol as a light-yellow solid, mp 214-215° C.

Workup

  1. customwere combined in a pressure vessel
  2. customfor 24 hours
  3. filtrationfiltered through CELITE
  4. filtrationfilter agent
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified via column chromatography on silica gel (eluting with 20-50% CMA/chloroform)
  7. concentrationconcentrated under reduced pressure
  8. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-fce06eb557ac4f77a017dc0412fa3c83
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

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