Water → HCID 178515061, compound

HRID 1822246Notes

Reaction equation

HRID 1822246 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[C:3]=1[C:19](=O)[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.O.[NH2:31][NH2:32].O>CN(C=O)C>[C:12]1([N:5]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]3[NH:31][N:32]=[C:19]([CH2:20][CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:3]=3[C:4]2=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 54676202HCID 54676202, compound

Product 1

HCID 178515061HCID 178515061, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 4-hydroxy-3-(1-oxo-4-phenylbutyl)-1-phenyl-1,8-naphthyridin-2 (1H)-one (384 mg, 11.0 mmol, prepared in Synthetic Example 30) in DMF (4 ml) was added hydrazine monohydrate (80%, 160 μl, 4.0 mmol, 4.0 eq.), and the mixture was stirred at 100 to 110° C. for 2 hours. The reaction mixture was admixed with water, and filtered to give precipitates which were washed with water and dried to afford 5-phenyl-3-(3-phenylpropyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (354 mg, 93%).

Workup

  1. filtrationfiltered
  2. customto give
  3. customprecipitates which
  4. washwere washed with water
  5. customdried

Sources & evidence

ORD record
ord-d53a4e727daa42d891721a2e095227e0
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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