HCID 23138739, compound → HCID 74020258, compound

HRID 1171708Notes

Reaction equation

HRID 1171708 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].C(S[CH:10]([C:36]1[CH:40]=[CH:39][N:38]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[N:37]=1)[C:11]1[CH2:16][N:15]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13][CH:12]=1)(=O)C>CS(C)=O.C(OCC)(=O)C>[C:1]([S:3][CH:12]1[CH2:13][CH2:14][N:15]([C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:16][C:11]1=[CH:10][C:36]1[CH:40]=[CH:39][N:38]([CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[N:37]=1)(=[O:4])[CH3:2]

Participants

5

Reactant 2

HCID 23138739HCID 23138739, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 74020258HCID 74020258, compoundYield 97.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Potassium thioacetate (5.91 g) was added to a solution of 5-((acetylsulfanyl){1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methyl)-1-(triphenylmethyl)-1,2,3,6-tetrahydropyridine (3.00 g), in dimethyl sulfoxide (30 ml). The mixture was stirred at 80° C. for 4 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate, and washed successively with water and a saturated aqueous sodium chloride solution. After the extract was dried over anhydrous sodium sulfate, it was concentrated under reduced pressure, and the residue was purified by silica gel chromatography using ethyl acetate and hexane (1:9 to 2:3) as eluents to afford a crude product of 4-(acetylsulfanyl)-3-({1-[2-(ethoxycarbonyl)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidine (2.93 g) as a mixture of geometric isomers.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed successively with water
  3. dry with materialAfter the extract was dried over anhydrous sodium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ec091a3395a40d6ba4c4b65b56f22a8
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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