Lawesson's reagent → 2-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-5-methyl-1,3,4-thiadiazole

HRID 397634Notes

Reaction equation

HRID 397634 reaction equation
COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:10])=CC=1.[C:23]([NH:26][NH:27][C:28]([C@@H:30]1[CH2:35][CH2:34][CH2:33][CH2:32][N:31]1[S:36]([C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)(=[O:38])=[O:37])=O)(=O)[CH3:24]>C1(C)C=CC=CC=1>[F:45][C:42]1[CH:43]=[CH:44][C:39]([S:36]([N:31]2[CH2:32][CH2:33][CH2:34][CH2:35][C@H:30]2[C:28]2[S:10][C:23]([CH3:24])=[N:26][N:27]=2)(=[O:38])=[O:37])=[CH:40][CH:41]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagent2×HCID 57053283N'2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazide

Product 1

HCID 98628332-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-5-methyl-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulphide] (271 mg) was added to a solution of N′2-acetyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbohydrazide (192 mg) [see Preparation 39] in toluene (10 ml). The reaction mixture was heated under reflux for 3 hours and the cooled mixture was then purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 30:70 (in 10% increments), by volume, hexane:ethyl acetate, to afford 2-[(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidyl]-5-methyl-1,3,4-thiadiazole (106 mg) as a clear oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customthe cooled mixture was then purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 30:70 (in 10% increments), by volume, hexane

Sources & evidence

ORD record
ord-c4ceab0dc095465ab6252732dbd5e521
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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