Hydrazine hydrate (1:1) → HCID 178514884, compound

HRID 217395Notes

Reaction equation

HRID 217395 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(=O)[C:3]=1[C:24](=O)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[CH:27]=1.O.[NH2:38][NH2:39].[C:40](=[O:43])([O-])O.[Na+]>CN(C=O)C>[F:20][C:19]([F:22])([F:21])[O:18][C:14]1[CH:13]=[C:12]([N:5]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]3[NH:38][N:39]=[C:24]([CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[CH:27]=4)[C:3]=3[C:40]2=[O:43])[CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 86630454HCID 86630454, compound

Product 1

HCID 178514884HCID 178514884, compoundYield 4.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a suspension of 4-hydroxy-1-(3-trifluoromethoxyphenyl)-3-(3-trifluoromethylphenylacetyl)-1,8-naphthyridin-2(1H)-one (254 mg, 0.50 mmol) produced in Synthesis Example 21 in DMF (5 mL) was added hydrazine monohydrate (purity of 80%, 97 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 5-(3-trifluoromethoxyphenyl)-3-(3-trifluoromethylbenzyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4(5H)-one (12 mg, yield 4.8%).

Workup

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

Sources & evidence

ORD record
ord-7f4d20f475a54aacbbe7b423f0fd7f08
Source dataset
uspto-grants-2012_06
Patent number
US08193356B2

Reaction notes

Loading…