Sodium Azide → 2-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carbonyl azide

HRID 1186763Notes

Reaction equation

HRID 1186763 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[N:11]([CH3:28])[C:12](=[O:27])[C:13]([CH3:26])=[CH:14][C:15]=1[C:16](ON1C(=O)CCC1=O)=[O:17].C1COCC1.CC(C)=O.[N-:38]=[N+:39]=[N-:40].[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[N:11]([CH3:28])[C:12](=[O:27])[C:13]([CH3:26])=[CH:14][C:15]=1[C:16]([N:38]=[N+:39]=[N-:40])=[O:17]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 22559816Acetone tetrahydrofuranHCID 866645042,5-Dioxopyrrolidin-1-yl 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

Product 1

HCID 866645052-(2-Fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carbonyl azideYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml round-bottom flask was charged with 2,5-dioxopyrrolidin-1-yl 2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (1.2 g, 2.40 mmol) and a mixture of THF/acetone (15 mL/30 mL). To the mixture was added NaN3 (0.52 g, 8 mmol) is previously dissolved in H2O (10 mL). The reaction mixture was stirred art room temperature for 16 hours and the organic solvents were removed under reduced pressure yielding to the desired product as a light brown solid (0.98 g, 96%).

Workup

  1. customthe organic solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-50d26c6e1f394fc1809b93c2d7e1e113
Source dataset
uspto-grants-2014_03
Patent number
US08673919B2

Reaction notes

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