Trifluoroacetic acid → N-[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]methyl]cyclopropanecarboxamide

HRID 383226Notes

Reaction equation

HRID 383226 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:29])([F:28])[F:27])[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]([CH:24]=O)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:30]1([C:33]([NH2:35])=[O:34])[CH2:32][CH2:31]1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:26]([F:28])([F:27])[F:29])[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]([CH2:24][NH:35][C:33]([CH:30]4[CH2:32][CH2:31]4)=[O:34])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 80376CyclopropanecarboxamideHCID 874797834-[5-(3,5-Dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxaldehyde

Product 1

HCID 25256552N-[[4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenyl]methyl]cyclopropanecarboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of the title compound of Step B (127 mg, 0.29 mmol), cyclopropanecarboxamide (74 mg, 0.87 mmol), trifluoroacetic acid (0.07 mL, 0.87 mmol) and triethylsilane (0.14 ml, 0.87 mmol) in toluene (2 mL) was gently refluxed overnight. The reaction mixture was then concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel using hexane/EtOAc as eluent to provide the title compound, a compound of this invention, as a white foamy solid (113 mg, 77% yield).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-78f8bfef94c645fdb22b6232d88b4a08
Source dataset
uspto-grants-2013_02
Patent number
US08367584B2

Reaction notes

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