Diisopropylethylamine → (E)-1-Isopropyl-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2-(trifluoromethyl)benzoyl)-N-(2,2,2-trifluoroethyl)hydrazinecarboxamide

HRID 1502784Notes

Reaction equation

HRID 1502784 reaction equation
CCN(C(C)C)C(C)C.F[P-](F)(F)(F)(F)F.CN(C(N(C)C)=[N+]1C2C(=NC=CC=2)[N+]([O-])=N1)C.Cl.[NH2:35][N:36]([CH:45]([CH3:47])[CH3:46])[C:37]([NH:39][CH2:40][C:41]([F:44])([F:43])[F:42])=[O:38].[F:48][C:49]([F:76])([F:75])[C:50]1[CH:58]=[C:57](/[CH:59]=[CH:60]/[CH:61]([C:66]2[CH:71]=[C:70]([Cl:72])[C:69]([Cl:73])=[C:68]([Cl:74])[CH:67]=2)[C:62]([F:65])([F:64])[F:63])[CH:56]=[CH:55][C:51]=1[C:52](O)=[O:53]>CN(C=O)C.O>[CH:45]([N:36]([C:37]([NH:39][CH2:40][C:41]([F:43])([F:42])[F:44])=[O:38])[NH:35][C:52](=[O:53])[C:51]1[CH:55]=[CH:56][C:57](/[CH:59]=[CH:60]/[CH:61]([C:66]2[CH:67]=[C:68]([Cl:74])[C:69]([Cl:73])=[C:70]([Cl:72])[CH:71]=2)[C:62]([F:63])([F:64])[F:65])=[CH:58][C:50]=1[C:49]([F:75])([F:76])[F:48])([CH3:47])[CH3:46]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 867225801-Amino-1-isopropyl-3-(2,2,2-trifluoroethyl)urea hydrochlorideHCID 867225822-(trifluoromethyl)-4-[(E)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl]benzoic acidHCID 178484293HCID 178484293, compound

Product 1

HCID 86722579(E)-1-Isopropyl-2-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)-2-(trifluoromethyl)benzoyl)-N-(2,2,2-trifluoroethyl)hydrazinecarboxamideYield 32.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (0.32 ml, 1.88 mmol), 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU) (263 mg, 0.69 mmol) and 1-amino-1-isopropyl-3-(2,2,2-trifluoroethyl)urea hydrochloride (178 mg, 0.75 mmol) were added to a stirred solution of 2-(trifluoromethyl)-4-[(E)-4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl]benzoic acid (300 mg, 0.63 mmol) in DMF (2 mL) at ambient temperature and the reaction mixture was stirred for 4 h. Water was added to the reaction mixture and it was extracted with EtOAc. The organic layer was washed with brine followed by water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography on silica, eluting with 20% EtOAc in petroleum ether to afford the title compound as a brown gum (135 mg, 29%).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica
  7. washeluting with 20% EtOAc in petroleum ether

Sources & evidence

ORD record
ord-53f873cd39454447bb976dcd8a4b09d6
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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