HCID 178514895, compound → HCID 178507538, compound

HRID 1822234Notes

Reaction equation

HRID 1822234 reaction equation
[N+:1]([C:4]1[CH:30]=[CH:29][C:7]([CH2:8][C:9]2[C:13]3[C:14](=[O:28])[N:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[N:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]=3[NH:11][N:10]=2)=[CH:6][CH:5]=1)([O-])=O>CN(C=O)C.CO.[C].[Pd]>[NH2:1][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][C:9]2[C:13]3[C:14](=[O:28])[N:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[C:16]4[N:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]=3[NH:11][N:10]=2)=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 178514895HCID 178514895, compound

Product 1

HCID 178507538HCID 178507538, compoundYield 65.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-nitrobenzyl)-5-phenyl-1H-pyrazolo [4,3-c][1,8]naphthyridin-4 (5H)-one (200 mg, 0.50 mmol, prepared in Example 24) in DMF (10 ml) and methanol (10 ml) was added activated carbon-palladium (20 mg), the mixture was stirred under hydrogen atmosphere for 3 days, 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-(4-aminobenzyl)-5-phenyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (120 mg, 65%).

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-afce37eb44c34e449a079205d671f136
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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