1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [2-(2,4-Difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester

HRID 10304

Reaktionsgleichung

Reaktionsgleichung von HRID 10304
[F:1][C:2]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:6]=1[C:7]([OH:9])=O.[C:21]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])(=[O:24])[NH:22][NH2:23].C(N=C=NCCCN(C)C)C>ClCCl>[C:26]([O:25][C:21]([N:22]([C:7](=[O:9])[C:6]1[CH:10]=[C:11]([F:15])[C:12]([F:14])=[CH:13][C:5]=1[NH:4][C:3]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:2]=1[F:1])[NH2:23])=[O:24])([CH3:29])([CH3:28])[CH3:27]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 149974752-(2,4-Difluoroanilino)-4,5-difluorobenzoic acid

Produkt 1

HCID 69071940[2-(2,4-Difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl esterAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid (Example 5, 2.18 g, 7.6 mmol) and tert-butyl carbazate (1.57 g, 11.8 mmol) in dichloromethane (30 mL) is added 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.25 g, 11.77 mmol). After stirring for 16 hours at room temperature, the reaction mixture is diluted with dichloromethane and then washed with saturated NaHCO3, water, and brine. The organic layer is dried over Na2SO4, concentrated under vacuum, and purified via column chromatography (1:3 ethyl acetate/hexanes) to afford [2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]-hydrazinecarboxylic acid tert-butyl ester as a solid (2.20 g). MS EI: m/z 400 (M+).

Aufarbeitung

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. custompurified via column chromatography (1:3 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-eeeb0d9ca8654a97b94c5952a45d29e4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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