Hydrazine hydrate (1:1) → HCID 178514880, compound

HRID 217397Notes

Reaction equation

HRID 217397 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]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=2)[C:4](=[O:23])[C:3]=1[C:24](=O)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1OC(F)(F)F.[OH2:38].[NH2:39][NH2:40].C(=O)([O-])O.[Na+]>CN(C=O)C>[F:20][C:19]([F:22])([F:21])[O:38][C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[CH2:25][C:24]1[C:3]2[C:4](=[O:23])[N:5]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:40][N:39]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 86630458HCID 86630458, compound

Product 1

HCID 178514880HCID 178514880, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 4-hydroxy-1-(3-trifluoromethoxyphenyl)-3-(2-trifluoromethoxyphenylacetyl)-1,8-naphthyridin-2(1H)-one (420 mg, 0.80 mmol) produced in Synthesis Example 23 in DMF (5 mL) was added hydrazine monohydrate (purity of 80%, 155 μL), and the mixture was stirred at 100 to 110° C. for 1 hour. To the reaction solution was added a sodium hydrogencarbonate aqueous solution. The resulting precipitate was separated by filtration, recrystallized from ethanol, and dried to give 3-(2-trifluoromethoxybenzyl)-5-(3-trifluoromethoxyphenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one (233 mg, yield 56%).

Workup

  1. customThe resulting precipitate was separated by filtration
  2. customrecrystallized from ethanol
  3. customdried

Sources & evidence

ORD record
ord-ba41a903604f41888a8c2731a36000a3
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

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