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 1502784ノート

反応式

HRID 1502784 の反応式
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]

参加物

7

反応物 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、化合物

生成物 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)hydrazinecarboxamide収率 32.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-53f873cd39454447bb976dcd8a4b09d6
出典データセット
uspto-grants-2015_12
特許番号
US09210927B2

反応ノート

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