Trifluoroacetamide → 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

HRID 467594

Reaction equation

HRID 467594 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:32]([F:35])([F:34])[F:33])[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][CH3:31])=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].ClC1C=C(C2(C(F)(F)F)ON=C(C3C4C(=CC=CC=4)C(C(NCCS(C)(=[N:66][C:67](=[O:72])[C:68]([F:71])([F:70])[F:69])=O)=O)=CC=3)C2)C=C(Cl)C=1.FC(F)(F)C(N)=O.C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:32]([F:33])([F:34])[F:35])[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]([CH3:31])=[N:66][C:67](=[O:72])[C:68]([F:71])([F:70])[F:69])=[O:26])=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 67717TrifluoroacetamideHCID 76724Iodobenzene diacetateHCID 251415254-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(S-methyl-N-(2,2,2-trifluoroacetyl)sulfonimidoyl)ethyl]-1-naphthalenecarboxamideHCID 866434244-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide

Product 1

HCID 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-carboxamideYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-[4,5-dihydro-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-(methylthio)ethyl]-1-naphthalenecarboxamide (prepared analogously as described for the compound of Example 3, Step A) (200 mg), 2,2,2-trifluoroacetamide (80 mg), MgO (57 mg), and Rh2(OAc)4 (4 mg) in dichloromethane (4 mL) was added PhI(OAc)2 (172 mg) at room temperature. The resulting mixture was stirred overnight at room temperature, then filtered through a short pad of Celite® diatomaceous filter aid, and rinsed with ethyl acetate. The filtrate was concentrated, and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetates (1:1 to 1:4) as eluent to afford the title compound as a semisolid (70 mg, 30% yield).

Workup

  1. customprepared analogously
  2. filtrationfiltered through a short pad of Celite®
  3. filtrationdiatomaceous filter aid
  4. washrinsed with ethyl acetate
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-9e20c2c69d1f4ebb8c8f3c835cbe4991
Source dataset
uspto-grants-2014_01
Patent number
US08623875B2

Linked notes

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