Hydrazine hydrate (1:1) → HCID 178422494, compound

HRID 217384Notes

Reaction equation

HRID 217384 reaction equation
O[C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:12])=[CH:9][CH:10]=2)[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[C:3]=1[C:20](=O)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O.[NH2:30][NH2:31].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:21]([C:20]1[C:3]2[C:4](=[O:19])[N:5]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]3[N:7]=[C:8]([CH3:12])[CH:9]=[CH:10][C:11]=3[C:2]=2[NH:31][N:30]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 68947924HCID 68947924, compound

Product 1

HCID 178422494HCID 178422494, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 4-hydroxy-7-methyl-1-phenyl-3-phenylacetyl-1,8-naphthyridin-2(1H)-one (370 mg, 1.0 mmol) produced in Synthesis Example 3 in DMF (8 mL) was added hydrazine monohydrate (purity of 80%, 160 μL), and the mixture was stirred at 100 to 110° C. for 2 hours. To the reaction solution was added a sodium hydrogencarbonate aqueous solution. The resulting precipitate was separated by filtration, washed with water, and dried to give 3-benzyl-7-methyl-5-phenyl-1H-pyrazolo [4,3-c][1,8]-naphthyridin-4(5H)-one as a form of crystal (281 mg, yield 83%).

Workup

  1. customThe resulting precipitate was separated by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-912f9d117d804387b09599abbf872c33
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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