Dimethyl Sulfoxide → HCID 86643425, compound

HRID 508133Notes

Reaction equation

HRID 508133 reaction equation
[CH3:1][S:2]([CH3:4])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Cl:18][C:19]1[CH:20]=[C:21]([C:26]2([C:44]([F:47])([F:46])[F:45])[O:30][N:29]=[C:28]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34]([C:41]([NH2:43])=[O:42])=[CH:33][CH:32]=3)[CH2:27]2)[CH:22]=[C:23]([Cl:25])[CH:24]=1>ClCCl>[Cl:18][C:19]1[CH:20]=[C:21]([C:26]2([C:44]([F:46])([F:45])[F:47])[O:30][N:29]=[C:28]([C:31]3[C:40]4[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:34]([C:41]([N:43]=[S:2]([CH3:4])[CH3:1])=[O:42])=[CH:33][CH:32]=3)[CH2:27]2)[CH:22]=[C:23]([Cl:25])[CH:24]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 9845Trifluoroacetic anhydrideHCID 68514582HCID 68514582, compound

Product 1

HCID 86643425HCID 86643425, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-60 °C

Procedure

To a stirred solution of dimethylsulfoxide (38 mg) in dichloromethane (1 mL) at −60° C. was added trifluoroacetic anhydride (105 mg). After the reaction mixture was stirred for 10 minutes at −60° C., a solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxamide (75 mg, in 1.5 mL of dichloromethane and 0.4 mL of dimethylsulfoxide) was added. The reaction mixture was allowed to warm to −20° C. over 1 h, then quenched with water and extracted with dichloromethane. The combined organic extract was washed with aqueous 1.0 N of NaOH and brine, dried with anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel using dichloromethane/methanol (98:2 to 95:5) as eluent to afford the title product, a compound of the present invention, as semi-solid (70 mg, 82% yield).

Workup

  1. temperatureto warm to −20° C. over 1 h
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. extractionThe combined organic extract
  5. washwas washed with aqueous 1.0 N of NaOH and brine
  6. dry with materialdried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f6f4f8c6e8ed439db03eb2259eb8c561
Source dataset
uspto-grants-2015_08
Patent number
US09095138B2

Reaction notes

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