Diisopropylethylamine → (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)-2-(trifluoromethoxy)benzamide

HRID 1502967Notes

Reaction equation

HRID 1502967 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:27]([F:30])([F:29])[F:28])/[CH:11]=[CH:12]/[C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[C:15]([O:22][C:23]([F:26])([F:25])[F:24])[CH:14]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].[NH2:31][CH2:32][C:33]([NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:34].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:27]([F:30])([F:29])[F:28])/[CH:11]=[CH:12]/[C:13]2[CH:21]=[CH:20][C:16]([C:17]([NH:31][CH2:32][C:33](=[O:34])[NH:35][CH2:36][C:37]([F:40])([F:39])[F:38])=[O:18])=[C:15]([O:22][C:23]([F:24])([F:25])[F:26])[CH:14]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 86675151(E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid

Product 1

HCID 86675150(E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)-2-(trifluoromethoxy)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-(trifluoromethoxy)benzoic acid (0.25 g, 0.52 mmol), 2-amino-N-(2,2,2-trifluoroethyl)acetamide (0.158 g, 0.62 mmol), PyBOP (0.40 g, 0.78 mmol) and DIPEA (0.134 g, 1.04 mmol) in CH2Cl2 (10.0 mL) were stirred at ambient temperature for 16 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; eluting with 20% ethyl acetate/pet ether) afforded the title compound as a pale yellow gummy material (0.15 g, 47%).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe combined CH2Cl2 layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification
  6. washby flash column chromatography (SiO2, 100-200 mesh; eluting with 20% ethyl acetate/pet ether)

Sources & evidence

ORD record
ord-74bbacb5f7fe4afda47261859ccf6226
Source dataset
uspto-grants-2015_12
Patent number
US09211281B2

Reaction notes

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