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 1502784노트

반응식

HRID 1502784 반응식
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]

참가 물질

7

반응물 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, 화합물

생성물 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)hydrazinecarboxamide수율 32.5%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-53f873cd39454447bb976dcd8a4b09d6
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09210927B2

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