HCID 178514922, compound → HCID 178507550, compound

HRID 1822206Notes

Reaction equation

HRID 1822206 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([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:6][CH:5]=1)([O-])=O>CN(C=O)C.CO.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([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:6][CH:5]=1

Participants

5

Reactant 1

HCID 178514922HCID 178514922, compound

Product 1

HCID 178507550HCID 178507550, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(4-nitrophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (131 mg, 0.32 mmol, prepared in Example 11) in DMF (4 ml) and methanol (4 ml) was added activated carbon-palladium (13 mg), and the mixture was stirred under hydrogen atmosphere for 3.5 hours, 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-(4-aminophenyl)ethyl]-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (113 mg, 93%).

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-88f31cdfb4364b2a89a91a4cb335d624
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

Loading…