HCID 178514919, compound → HCID 178507493, compound

HRID 1822228Notes

Reaction equation

HRID 1822228 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1[C:16]2[C:17](=[O:31])[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[N:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:15]=2[NH:14][N:13]=1)([O-])=O>CN(C=O)C.CO.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12]1[C:16]2[C:17](=[O:31])[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[N:20]=[CH:21][CH:22]=[CH:23][C:24]=3[C:15]=2[NH:14][N:13]=1

Participants

5

Reactant 1

HCID 178514919HCID 178514919, compound

Product 1

HCID 178507493HCID 178507493, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(2-nitrophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (420 mg, 11.0 mmol, prepared in Example 16) in DMF (45 ml) and methanol (20 ml) was added activated carbon-palladium (45 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-(2-aminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]-naphthyridin-4 (5H)-one (364 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-0bc943d37e994f8f80582ae77ecf91b9
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…