Potassium Carbonate → HCID 67363972, compound

HRID 2407167Notes

Reaction equation

HRID 2407167 reaction equation
CS(O[C:6]1[N:7]=[C:8]([S:20][CH3:21])[N:9]=[N:10][C:11]=1[C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=1)(=O)=O.C([O-])([O-])=O.[K+].[K+].[CH3:28][CH:29]1[CH2:34][CH2:33][CH2:32][NH:31][CH2:30]1.C(OCC)(=O)C.CCCCCC>O1CCOCC1.O>[Cl:19][C:14]1[CH:13]=[C:12]([C:11]2[N:10]=[N:9][C:8]([S:20][CH3:21])=[N:7][C:6]=2[N:31]2[CH2:32][CH2:33][CH2:34][CH:29]([CH3:28])[CH2:30]2)[CH:17]=[C:16]([Cl:18])[CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 790813-MethylpiperidineHCID 21226206Ethyl acetate hexaneHCID 86676121HCID 86676121, compound

Product 1

HCID 67363972HCID 67363972, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A crude solution of 6-(3,5-dichlorophenyl)-3-(methylsulfanyl)-1,2,4-triazin-5-yl methanesulfonate (5.43 mmol) in dioxane (3 mL), was treated with K2CO3 (1.0 g, 7.2 mmol) and 3-methyl piperidine (1.68 g, 16.9 mmol), and the resulting mixture was stirred at room temperature overnight. After completion of the reaction (TLC, ethyl acetate/hexane, 1:1), the mixture was poured into water (25 mL) and extracted with DCM or ethyl acetate (3×25 ml). The combined organic extracts were then dried over Na2SO4, concentrated in vacuo and purified by flash chromatography, eluting with 15% ethyl acetate in hexane to afford 6-(3,5-dichlorophenyl)-5-(3-methylpiperidin-1-yl)-3-(methylsulfanyl)-1,2,4-triazine (0.8 g, 40%).

Workup

  1. extractionextracted with DCM or ethyl acetate (3×25 ml)
  2. dry with materialThe combined organic extracts were then dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography
  5. washeluting with 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-9032e03da6f24cb580800fb2af4432a1
Source dataset
uspto-grants-2014_08
Patent number
US08809525B2

Reaction notes

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