Dichloromethane → HCID 9798650, compound

HRID 1108563Notes

Reaction equation

HRID 1108563 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][NH:20][C:21](=O)[CH3:22])[O:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1.ClCCl>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[CH2:18][CH:17]([CH2:19][NH:20][C:21](=[S:33])[CH3:22])[O:16][N:15]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 87949Lawesson's reagentHCID 9927774HCID 9927774, compound

Product 1

HCID 9798650HCID 9798650, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

1.0 g (3.0 mmole) of N-({3-[3-fluoro-4-(4-thiomorpholinyl)phenyl]-4,5-dihydro-5-isoxazolyl}methyl)acetamide is suspended in 12 ml dioxane in a 50 ml one neck round bottom flask under nitrogen. The suspension is treated with Lawesson's Reagent (1.27 g, 3.15 mmole) and the reaction is stirred at 80° C. for 1 hour. The mixture is cooled to room temperature, brought to homogeneity with dichloromethane and is treated with 10 g silica gel (230-400 mesh) and is concentrated to dryness. The plug is loaded onto a SIM and the material is chromatographed twice over 40 g silica gel (BIOTAGE), eluting with 7% acetone/dichloromethane while collecting 25 ml fractions. Fractions 6-13 are combined and concentrated to afford 902 mg (85%) of the title compound as a solid. mp=219-220° C.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. additionis treated with 10 g silica gel (230-400 mesh)
  3. concentrationis concentrated to dryness
  4. customthe material is chromatographed twice over 40 g silica gel (BIOTAGE)
  5. washeluting with 7% acetone/dichloromethane
  6. customwhile collecting 25 ml fractions
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f820f081fb01455b817490426d07a45b
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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