Reaction #44203

Reaction equation

HCl

Ethyl acetimidate HCl salt

Et3N

4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide

→

desired product

4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid N′-(1-imino-ethyl)-hydrazide

Solvents

THF

DMF

Conditions

Workup

1. 1
   Otherat 0° C
2. 2
   workup.ADDITION17 hours at room temperature, the reaction mixture was poured onto water
3. 3
   Extractionextracted with ethyl acetate
4. 4
   DryingThe combined organic extracts were dried (MgSO4)
5. 5
   Concentrationconcentrated under reduced pressure

Procedure

Ethyl acetimidate HCl salt (40 mg, 0.32 mmol) and Et3N (0.049 mL, 0.35 mmol) were added to a stirred suspension of 4-(4-bromo-2-fluorophenylamino)-5-fluoro-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid hydrazide (0.10 g, 0.27 mmol) in 2:1 THF:DMF (3 mL) at 0° C. After 1.5 hours at 0° C. and 17 hours at room temperature, the reaction mixture was poured onto water, neutralized with dilute aqueous HCl and extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. Trituration with methylene chloride gave the desired product.

Source