Hydrazine hydrate (1:1) → HCID 178514901, compound

HRID 217414Notes

Reaction equation

HRID 217414 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][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.O.[NH2:29][NH2:30].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:29][N:30]=[C:19]([CH2:20][CH:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[C:3]=3[C:4]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 68947970HCID 68947970, compound

Product 1

HCID 178514901HCID 178514901, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 4-hydroxy-1-phenyl-3-(tetrahydro-2H-pyran-4-ylacetyl)-1,8-naphthyridin-2(1H)-one (120 mg, 0.33 mmol) produced in Synthesis Example 40 in DMF (2 mL) was added hydrazine monohydrate (purity of 80%, 53 μL), and the mixture was stirred at 110to 120° C. for 2 hours. To the reaction solution was added a sodium hydrogen carbonate aqueous solution. The resulting precipitate was separated by filtration, washed with water, and dried to give 5-phenyl-3-(tetrahydro-2H-pyran-4-ylmethyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one as a form of crystal (66 mg, yield 55%).

Workup

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

Sources & evidence

ORD record
ord-3de55fb0d092479683e69fa22f3a2528
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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