Reaction #710486

Reaction equation

normal propyl isocyanate

N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide

potassium-t-butoxide

→

N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-((propylcarbamoyl)oxy)acetimidamide

Yield 32.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Concentrationthe reaction solution was concentrated under reduced pressure, and ethyl acetate
3. 3
   workup.ADDITIONa saturated saline solution were added
4. 4
   Otherliquid separation
5. 5
   DryingThe ethyl acetate layer was dried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   Otherpurified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3)
8. 8
   Otherto obtain the subject material
9. 9
   OtherAmount obtained 16 mg (yield 32%)

Procedure

5 ml of anhydrous acetonitrile was added to 11 mg (0.13 mmol) of normal propyl isocyanate, 40 mg (0.12 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoro-N′-hydroxyacetimidamide (1-499) synthesized by the method in Synthetic Example 7 and 4 mg (0.04 mmol) of potassium-t-butoxide were added thereto, and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, the reaction solution was concentrated under reduced pressure, and ethyl acetate and a saturated saline solution were added thereto to perform liquid separation. The ethyl acetate layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified by a TLC plate (one sheet of 0.5 mm plate, evolved with hexane:ethyl acetate=1:3) to obtain the subject material. Amount obtained 16 mg (yield 32%).

Source