Triphenylphosphine → 5-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone

HRID 721975Notes

Reaction equation

HRID 721975 reaction equation
N(C(OCC)=O)=NC(OCC)=O.O[CH:14]1[S:18][CH2:17][N:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)[C:15]1=[O:29].[CH3:30][C:31]([C:34]1[CH:38]=[CH:37][NH:36][N:35]=1)([CH3:33])[CH3:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH3:30][C:31]([C:34]1[CH:38]=[CH:37][N:36]([CH:14]2[S:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[C:15]2=[O:29])[N:35]=1)([CH3:33])[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 218819855-Hydroxy-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinoneHCID 178441177HCID 178441177, compound

Product 1

HCID 218819915-[3-(1,1-dimethylethyl)-1H-pyrazol-1-yl]-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To tetrahydrofuran (15 mL) at about −10° C. stirred under a nitrogen atmosphere were added diethyl azodicarboxylate (0.66 mL, 4.18 mmol), 5-hydroxy-3-[3-(trifluoromethyl)phenyl]-4-thiazolidinone (1 g, 3.8mmol), 3-(1,1-dimethylethyl)-1H-pyrazole (0.48 g, 3.8 mmol) and triphenylphosphine (1.2 g, 4.41 mmol). After the addition, the reaction mixture was allowed to warm up to room temperature, and stirred overnight under a nitrogen atmosphere. The reaction mixture was concentrated, and the residue taken into a small amount of methylene chloride and then filtered. The filtrate was loaded on silica gel in a medium pressure liquid chromatography column and eluted with a solution of 20% ethyl acetate and 80% hexanes followed by a solution of 33% ethyl acetate and 67% hexanes to give 0.26 g of a crude product. The crude product was further purified by medium pressure liquid chromatography (silica gel, 9% ethyl acetate/91% hexanes) to afford the title compound, a compound of this invention, as a viscous oil (130 mg).

Workup

  1. additionAfter the addition
  2. concentrationThe reaction mixture was concentrated
  3. filtrationfiltered
  4. washeluted with a solution of 20% ethyl acetate and 80% hexanes
  5. customto give 0.26 g of a crude product
  6. customThe crude product was further purified by medium pressure liquid chromatography (silica gel, 9% ethyl acetate/91% hexanes)

Sources & evidence

ORD record
ord-8102611fa94144258f8f7ff4b31debb8
Source dataset
uspto-grants-2006_11
Patent number
US07138361B2

Reaction notes

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