HCID 178514920, compound → HCID 178507553, compound

HRID 1822227Notes

Reaction equation

HRID 1822227 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]2[C:16]3[C:17](=[O:31])[N:18]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[N:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[NH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CN(C=O)C.CO.[C].[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]2[C:16]3[C:17](=[O:31])[N:18]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)[C:19]4[N:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:15]=3[NH:14][N:13]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 178514920HCID 178514920, compound

Product 1

HCID 178507553HCID 178507553, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(3-nitrophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (216 mg, 0.52 mmol, prepared in Example 15) in DMF (5 ml) and methanol (5 ml) was added activated carbon-palladium (22 mg), and the mixture was stirred overnight under hydrogen atmosphere, and filtered. After methanol was distilled off, the resultant solution was admixed with water, and filtered to give precipitates which were dried to afford 3-[2-(3-aminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]-naphthyridin-4 (5H)-one (189 mg, 94%).

Workup

  1. filtrationfiltered
  2. distillationAfter methanol was distilled off
  3. filtrationfiltered
  4. customto give
  5. customprecipitates which
  6. customwere dried

Sources & evidence

ORD record
ord-bfbb5a19e8514c648e2c7dede220f922
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…