Methylamine → HCID 89778659, compound

HRID 623302Notes

Reaction equation

HRID 623302 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[N:15][C:16](=S)[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1.[CH3:22][NH2:23]>CO.C(=O)([O-])[O-].[Ag+2]>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[N:15][C:16](=[N:23][CH3:22])[C:17]([F:20])([F:19])[F:18])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 71698838HCID 71698838, compound

Product 1

HCID 89778659HCID 89778659, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

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%).

Workup

  1. customwas returned to room temperature
  2. filtrationsubjected to suction filtration
  3. customto remove insoluble materials
  4. additionEthyl acetate and water were added
  5. customliquid separation
  6. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. custompurified with silica gel column chromatography (hexane:ethyl acetate=1:1)
  9. customto obtain the subject material
  10. customAmount obtained 81 mg (yield 56%)

Sources & evidence

ORD record
ord-1c8c215b96ee401e8c0509d9256a7f4f
Source dataset
uspto-grants-2016_04
Patent number
US09301525B2

Reaction notes

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