Reaction #710484

Reaction equation

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

methylamine

→

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

Yield 56.0%

Solvents

methanol

Conditions

Workup

1. 1
   Otherwas returned to room temperature
2. 2
   Filtrationsubjected to suction filtration
3. 3
   Otherto remove insoluble materials
4. 4
   workup.ADDITIONEthyl acetate and water were added
5. 5
   Otherliquid separation
6. 6
   Dryingthe organic layer was dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   Otherpurified with silica gel column chromatography (hexane:ethyl acetate=1:1)
9. 9
   Otherto obtain the subject material
10. 10
    OtherAmount obtained 81 mg (yield 56%)

Procedure

150 mg (0.45 mmol) of the N-[1-((6-chloropyridin-3-yl)methyl)pyridin-2(1H)-ylidene]-2,2,2-trifluoroethanethioamide (1-20) synthesized by the method in Synthetic Example 4 was dissolved in 5 ml of methanol, 105 μl (42 mg, 1.36 mmol) of methylamine (40% methanol solution) and 124 mg (0.45 mmol) of silver carbonate were added thereto, and the resulting mixture was stirred at 50° C. for 1 hour. After the reaction was completed, the reaction solution was returned to room temperature and subjected to suction filtration by using celite to remove insoluble materials. Ethyl acetate and water were added thereto to perform liquid separation, and the organic layer was dried over anhydrous magnesium sulfate, then concentrated under reduced pressure and purified with silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain the subject material. Amount obtained 81 mg (yield 56%).

Source