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Potassium Carbonate → 4-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(S-methylsulfinimidoyl)ethyl]-1-naphthalenecarboxamide

HRID 508132
Notes
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Reaction equation

HRID 508132 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:39]([F:42])([F:41])[F:40])[O:14][N:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]([NH:27][CH2:28][CH2:29][S:30]([CH3:38])=[N:31]C(=O)C(F)(F)F)=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:39]([F:40])([F:42])[F:41])[O:14][N:13]=[C:12]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([C:25]([NH:27][CH2:28][CH2:29][S:30]([CH3:38])=[NH:31])=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 866434234-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[S-methyl-N-(2,2,2-trifluoroacetyl)sulfinimidoyl]ethyl]-1-naphthalene-carboxamide2×

Product 1

HCID 743946104-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(S-methylsulfinimidoyl)ethyl]-1-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

To a stirred solution of 4-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[S-methyl-N-(2,2,2-trifluoroacetyl)sulfinimidoyl]ethyl]-1-naphthalene-carboxamide (70 mg) (i.e. the title compound of Step A) in methanol (2 mL) was added potassium carbonate (300 mg) at room temperature. After stirring overnight at room temperature, the reaction mixture was filtered through a short pad of silica gel and rinsed with ethyl acetate. After concentration, the residue was purified by column chromatography on silica gel using dichloromethane/methanol (98:2 to 92:8) as eluent to afford the title compound, a compound of the present invention, as a semisolid (9 mg, 15% yield).

Workup

  1. filtrationthe reaction mixture was filtered through a short pad of silica gel
  2. washrinsed with ethyl acetate
  3. concentrationAfter concentration
  4. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-a833238f74584be58378db75828d8403
Source dataset
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09095138B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes