Lawesson's reagent → HCID 56650967, compound

HRID 1961556Notes

Reaction equation

HRID 1961556 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:31]([F:34])([F:33])[F:32])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([F:30])[CH2:24][N:23]([C:25](=O)[CH:26]([CH3:28])[CH3:27])[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:31]([F:34])([F:33])[F:32])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4([F:30])[CH2:24][N:23]([C:25](=[S:44])[CH:26]([CH3:28])[CH3:27])[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57489445HCID 57489445, compound

Product 1

HCID 56650967HCID 56650967, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-(3-(4-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)phenyl)-3-fluoroazetidin-1-yl)-2-methylpropan-1-one (500 mg, 1.9 mmol) was dissolved in toluene (35 mL). Lawesson's reagent (790 mg, 1.9 mmol) was added and the reaction mixture was heated to reflux for 2 hours, then cooled to room temperature and allowed to stir overnight. The reaction mixture was filtered and the filtrate was concentrated under vacuum. The crude residue from the filtrate was chromatographed (40 g Redi-Sep column) eluting from 100% heptane to 25:75 EtOAc:heptane to afford the product (415 mg, 80%) as a solid. 1HNMR (CDCl3): 7.77 (2H), 7.61 (2H), 7.54 (2H), 4.68 (4H), 4.12 (1H), 3.72 (1H), 2.88 (1H), 1.28 (6H); m/z (Cl) 537 ([M+H]+.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude residue from the filtrate was chromatographed (40 g Redi-Sep column)
  6. washeluting from 100% heptane to 25:75 EtOAc

Sources & evidence

ORD record
ord-f0e5c272729a4230b6fd85c85b1da247
Source dataset
uspto-grants-2013_04
Patent number
US08415310B2

Reaction notes

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