Sodium Hydroxide → 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-4-methyl-2,4-dihydro-[1,2,4]triazol-3-one

HRID 658391Notes

Reaction equation

HRID 658391 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:23]=[N:22][CH:21]=[CH:20][C:11]=1[C:12]([NH:14][NH:15][C:16]([NH:18][CH3:19])=[O:17])=O.[OH-].[Na+]>O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:23]=[N:22][CH:21]=[CH:20][C:11]=1[C:12]1[N:18]([CH3:19])[C:16](=[O:17])[NH:15][N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 590268142-(3-(2-fluoro-4-iodophenylamino)isonicotinoyl)-N-methylhydrazinecarboxamide

Product 1

HCID 590268295-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-4-methyl-2,4-dihydro-[1,2,4]triazol-3-oneYield 6.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-{3-[(2-fluoro-4-iodophenyl)amino]isonicotinoyl}-N-methylhydrazinecarboxamide (165 mg; 0.38 mmol) in water (3 mL) was added 1N NaOH (3 mL). The mixture became homogeneous. The reaction mixture was heated at 120° C. for 3 days. The progress of the reaction was monitored by LCMS. Concentration of the solvent and repeated purifications gave 10 mg of 5-[3-(2-Fluoro-4-iodo-phenylamino)-pyridin-4-yl]-4-methyl-2,4-dihydro-[1,2,4]triazol-3-one

Sources & evidence

ORD record
ord-7ce9895a836743e8a860a3527ad0d2af
Source dataset
uspto-grants-2011_12
Patent number
US08076486B2

Reaction notes

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