Diisopropylethylamine → (E)-2-Bromo-N'-methyl-N'-propionyl-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzohydrazide

HRID 1502922ノート

反応式

HRID 1502922 の反応式
[Br:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=2)[C:14]([F:17])([F:16])[F:15])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].[CH3:27][N:28]([C:30](=[O:33])[CH2:31][CH3:32])[NH2:29].CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C>ClCCCl.CN(C1C=CN=CC=1)C.O>[Br:1][C:2]1[CH:10]=[C:9](/[CH:11]=[CH:12]/[CH:13]([C:18]2[CH:19]=[C:20]([Cl:26])[C:21]([Cl:25])=[C:22]([Cl:24])[CH:23]=2)[C:14]([F:17])([F:15])[F:16])[CH:8]=[CH:7][C:3]=1[C:4]([NH:29][N:28]([CH3:27])[C:30](=[O:33])[CH2:31][CH3:32])=[O:5]

参加物

8

反応物 4

HCID 81531DiisopropylethylamineHCID 542680N-methylpropionohydrazideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86722549(E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-enyl)benzoic acid

生成物 1

HCID 86722548(E)-2-Bromo-N'-methyl-N'-propionyl-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl)but-1-en-1-yl)benzohydrazide

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 111,2-Dichloroethane溶媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

To a stirred solution of (E)-2-bromo-4-(4,4,4-trifluoro-3-(3,4,5-trichlorophenyl) but-1-enyl)benzoic acid (200 mg, 0.41 mmol) in 1,2-dichloroethane (DCE) (10 mL) was added N-methylpropionohydrazide (WO 2009110510) (50 mg, 0.49 mmol), DMAP (55 mg, 0.45 mmol), EDC.HCl (60 mg, 0.41 mmol) and DIPEA (0.20 mL, 1.1 mmol). The reaction mixture was stirred at 25° C. for 12 h, diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh) eluting with 30% EtOAc in hexane afforded the title compound as an off white solid (86 mg, 34%).

後処理

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash column chromatography (SiO2, 100-200 mesh)
  6. washeluting with 30% EtOAc in hexane

出典と根拠

ORDレコード
ord-1a37119d4721494abf3fbea94264e03c
出典データセット
uspto-grants-2015_12
特許番号
US09211280B2

反応ノート

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