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

HRID 508130Notes

Reaction equation

HRID 508130 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:39]([F:42])([F:41])[F:40])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([NH:26][CH2:27][CH2:28][S:29]([CH3:38])(=[N:31]C(=O)C(F)(F)F)=[O:30])=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:39]([F:40])([F:42])[F:41])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]([NH:26][CH2:27][CH2:28][S:29]([CH3:38])(=[NH:31])=[O:30])=[O:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 251415254-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(S-methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl)ethyl]-1-naphthalenecarboxamide

Product 1

HCID 743946094-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(S-methylsulfonimidoyl)ethyl]-1-naphthalenecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-[S-methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl]ethyl]-1-naphthalenecarboxamide (i.e. the title compound of Example 3) (60 mg) in methanol (4 mL) was added potassium carbonate (230 mg) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was filtered through a short pad of silical 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 provide the title product, a compound of the present invention, as a white solid (39 mg, 76% yield).

Sources & evidence

ORD record
ord-7c07a0ad40a1404f9075fcca863d77b4
Source dataset
uspto-grants-2015_08
Patent number
US09095138B2

Reaction notes

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