Ethanamine, 2,2,2-trifluoro- → 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide

HRID 541084Notes

Reaction equation

HRID 541084 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[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]([C:24]([O:26]C)=O)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.CCCP(=O)=O.[F:38][C:39]([F:43])([F:42])[CH2:40][NH2:41]>CN(C)C1C=CN=CC=1.ClCCl>[Cl:8][C:6]1[CH:5]=[C:4]([C:9]2([C:28]([F:30])([F:31])[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]([C:24]([NH:41][CH2:40][C:39]([F:43])([F:42])[F:38])=[O:26])=[CH:16][CH:15]=3)[CH2:10]2)[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

6

Reactant 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 16167369Propylphosphoric anhydrideHCID 58338637Methyl 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylate

Product 1

HCID 162202114-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-(2,2,2-trifluoroethyl)-1-naphthalenecarboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(bifluoromethyl)-3-isoxazolyl]-1-naphthalenecarboxylic acid (i.e. the product from Step C) (190 mg, 0.42 mmol), 4-(dimethylamino)pyridine (77 mg, 0.63 mmol), propylphosphonic anhydride (0.38 mL, 0.63 mmol, 50% in ethyl acetate) and 2,2,2-trifluoroethylamine (0.033 mL, 0.42 mL) in dichloromethane (5 mL) was stirred at room temperature overnight. The reaction mixture was concentrated, and the residue was purified by column chromatography on silica gel using hexanes/ethyl acetate as eluent to give the title product, a compound of the present invention, as a white solid (71 mg).

Workup

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

Sources & evidence

ORD record
ord-2558ca5335a54132a7b2fb01502bce61
Source dataset
uspto-grants-2014_10
Patent number
US08871941B2

Reaction notes

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