Water → HCID 178509827, compound

HRID 1822244Notes

Reaction equation

HRID 1822244 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][N:17]=3)[C:12](O)=[C:11]([C:20](=O)[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:10]2=[O:29])[CH:6]=[CH:7][CH:8]=1)#[N:2].O.[NH2:31][NH2:32].O>CN(C=O)C>[CH2:21]([C:20]1[C:11]2[C:10](=[O:29])[N:9]([C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=3)[C:18]3[N:17]=[CH:16][CH:15]=[CH:14][C:13]=3[C:12]=2[NH:32][N:31]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 54676179HCID 54676179, compound

Product 1

HCID 178509827HCID 178509827, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 1-(3-cyanophenyl)-4-hydroxy-3-(1-oxo-2-phenylethyl)-1,8-naphthyridin-2 (1H)-one (314 mg, 0.82 mmol, prepared in Synthetic Example 29) in DMF (4 ml) was added hydrazine monohydrate (80%, 132 μl, 4.12 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 3-benzyl-5-(3-cyanophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (287 mg, 92%).

Workup

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

Sources & evidence

ORD record
ord-29588d0601e54464aba66e742e046b13
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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