Lawesson's reagent → t-butyl 2-[4-(trifluoromethyl)phenyl]-6,7-dihydro[1,3]thiazolo[4,5-c]pyridin-5(4H)-carboxylate

HRID 1360174Notes

Reaction equation

HRID 1360174 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[NH:15][C:16](=O)[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1(C)C=CC=CC=1>[F:24][C:23]([F:26])([F:25])[C:20]1[CH:21]=[CH:22][C:17]([C:16]2[S:37][C:2]3[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][C:3]=3[N:15]=2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 66969913t-Butyl 4-oxo-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate2×

Product 1

HCID 66969278t-butyl 2-[4-(trifluoromethyl)phenyl]-6,7-dihydro[1,3]thiazolo[4,5-c]pyridin-5(4H)-carboxylateYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.40 g (1.0 mmol) of t-butyl 4-oxo-3-{[4-(trifluoromethyl)benzoyl]amino}piperidin-1-carboxylate (product of step 2) was dissolved in 0.47 g (1.2 mmol) of Lawesson's reagent, and the resulting solution was stirred under refluxing of 30 mL of toluene for 4 hours and distilled off under reduced pressure. The residue was purified by column chromatography to give 0.30 g (0.91 mmol) of the title compound in a total yield of 91%.

Workup

  1. distillationdistilled off under reduced pressure
  2. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-64be691be31f40d9b76b59d4a6345f18
Source dataset
uspto-grants-2011_02
Patent number
US07879848B2

Reaction notes

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