Water → (E)-N'-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)cyclopropanecarbohydrazide

HRID 587274ノート

反応式

HRID 587274 の反応式
[F:1][C:2]([F:24])([F:23])[CH:3]([C:14]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[C:16]([Cl:22])[CH:15]=1)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH2:13])=[CH:8][CH:7]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl.[CH:57]1([C:60](Cl)=[O:61])[CH2:59][CH2:58]1>C(Cl)Cl.C([O-])(O)=O.[Na+]>[F:24][C:2]([F:1])([F:23])[CH:3]([C:14]1[CH:15]=[C:16]([Cl:22])[C:17]([Cl:21])=[C:18]([Cl:20])[CH:19]=1)/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([NH:12][NH:13][C:60]([CH:57]2[CH2:59][CH2:58]2)=[O:61])=[CH:8][CH:7]=1

参加物

9

反応物 6

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86675193(E)-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)hydrazine

生成物 1

HCID 86675211(E)-N'-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)cyclopropanecarbohydrazide収率 55%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a stirred solution of (E)-(4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)phenyl)hydrazine (0.1 g, 0.3 mmol) in CH2Cl2 (10 mL) was added DIPEA (65 mg, 0.51 mmol), HOBt.H2O (59 mg, 0.38 mmol), EDC.HCl (73 mg, 0.38 mmol) and cyclopropanecarbonyl chloride (0.024 g, 0.28 mmol), and the reaction mixture was stirred at ambient temperature for 1 h. The reaction mixture was diluted with satd aq NaHCO3 solution and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (SiO2; 5-25% EtOAc in petroleum ether) afforded the title compound as a solid (65 mg, 55%): mp 138-140° C.; 1H NMR (400 MHz, CDCl3) δ 9.81 (s, 1H), 7.90 (s, 1H), 7.84 (s, 2H), 7.34 (d, J=8.4 Hz, 2H), 6.65 (d, J=15.6 Hz, 1H), 6.61 (m, 1H), 6.57 (s, 1H), 6.48 (dd, J=15.6, 8.8 Hz, 1H), 4.74 (m, 1H), 1.64 (m, 1H), 0.75 (m, 4H); ESIMS m/z 461.32 ([M−H]−).

後処理

  1. extractionextracted with CH2Cl2
  2. washThe combined CH2Cl2 layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (SiO2; 5-25% EtOAc in petroleum ether)

出典と根拠

ORDレコード
ord-e8029bfca3f94005859796289c38b437
出典データセット
uspto-grants-2016_01
特許番号
US09226500B2

反応ノート

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