Hydrazine hydrate (1:1) → HCID 178438928, compound

HRID 217413Notes

Reaction equation

HRID 217413 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)[CH:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:21][CH3:22].O.[NH2:31][NH2:32].C(=O)([O-])O.[Na+]>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]([CH:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:21][CH3:22])[C:3]=3[C:4]2=[O:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 689479984-hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one

Product 1

HCID 178438928HCID 178438928, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
115 °C

Procedure

To a suspension of 4-hydroxy-1-phenyl-3-(2-phenylbutyryl)-1,8-naphthyridin-2(1H)-one (98 mg, 0.25 mmol) produced in Synthesis Example 39 in DMF (2 mL) was added hydrazine monohydrate (purity of 80%, 40 μL), and the mixture was stirred at 110 to 120° C. for 2 hours. To the reaction solution was added a sodium hydrogencarbonate aqueous solution. The resulting precipitate was separated by filtration and washed with water. The precipitate was recrystallized from ethanol and diisopropyl ether to give 5-phenyl-3-(1-phenylpropyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one as a form of crystal (51 mg, yield 53%).

Workup

  1. customThe resulting precipitate was separated by filtration
  2. washwashed with water
  3. customThe precipitate was recrystallized from ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-f82997cb758b491581a1620a287c02a0
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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