Lawesson's reagent → HCID 86660505, compound

HRID 2199176Notes

Reaction equation

HRID 2199176 reaction equation
COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:10]2)=CC=1.[F:23][CH:24]([F:56])[C:25]1[CH:29]=[C:28]([CH:30]([F:32])[F:31])[N:27]([CH2:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([C:42]3[S:43][CH:44]=[C:45]([C:47](=[O:55])[CH2:48][CH:49]4[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]4)[N:46]=3)[CH2:38][CH2:37]2)=O)[N:26]=1>C1(C)C=CC=CC=1>[F:23][CH:24]([F:56])[C:25]1[CH:29]=[C:28]([CH:30]([F:32])[F:31])[N:27]([CH2:33][C:34]([N:36]2[CH2:41][CH2:40][CH:39]([C:42]3[S:43][CH:44]=[C:45]([C:47](=[O:55])[CH2:48][CH:49]4[CH2:54][CH2:53][CH2:52][CH2:51][CH2:50]4)[N:46]=3)[CH2:38][CH2:37]2)=[S:10])[N:26]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67466639HCID 67466639, compound

Product 1

HCID 86660505HCID 86660505, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

At room temperature, 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide (194 mg) was added to a solution of 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(cyclohexylacetyl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone (200 mg) in toluene (2 ml). The reaction mixture was stirred at 60° C. for 2 hours. After removal of the solvent under reduced pressure, the residue was purified chromatographically. This gave 1-[2-(1-{2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]ethanethioyl}-piperidin-4-yl)-1,3-thiazol-4-yl]-2-cyclohexylethanone (101 mg, 49%).

Workup

  1. customAfter removal of the solvent under reduced pressure
  2. customthe residue was purified chromatographically

Sources & evidence

ORD record
ord-94730d9d3bb0476fb0ae9e502f9a3e41
Source dataset
uspto-grants-2016_06
Patent number
US09357779B2

Reaction notes

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