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

HRID 10305

Reaktionsgleichung

Reaktionsgleichung von HRID 10305
[Cl:1][C:2]1[C:3]([NH:13][CH:14]2[CH2:16][CH2:15]2)=[C:4]([CH:8]=[C:9]([F:12])[C:10]=1[F:11])[C:5]([OH:7])=O.[C:17]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])(=[O:20])[NH:18][NH2:19].C(N=C=NCCCN(C)C)C>ClCCl>[C:22]([O:21][C:17]([N:18]([C:5](=[O:7])[C:4]1[CH:8]=[C:9]([F:12])[C:10]([F:11])=[C:2]([Cl:1])[C:3]=1[NH:13][CH:14]1[CH2:16][CH2:15]1)[NH2:19])=[O:20])([CH3:25])([CH3:24])[CH3:23]

Komponenten

5

Edukt 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 219789333-Chloro-2-cyclopropylamino-4,5-difluorobenzoic acid

Produkt 1

HCID 86591203(3-Chloro-2-cyclopropylamino-4,5-difluorobenzoyl)-hydrazinecarboxylic acid tert-butyl esterAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 3-chloro-2-cyclopropylamino-4,5-difluorobenzoic acid (Example 5d, 2.09 g, 8.45 mmol) in dichloromethane (30 mL) is added tert-butyl carbazate (1.67 g, 12.7 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (2.43 g, 12.7 mmol). After 16 hours, the reaction mixture is diluted with dichloromethane and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4 and filtered. The filtrate is concentrated under vacuum and purified via flash column chromatography (1:2 ethyl acetate/hexanes) to afford the title compound (1.93 g). MS EI: m/z 360 (M+).

Aufarbeitung

  1. washwashed with saturated NaHCO3, water, and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under vacuum
  5. custompurified via flash column chromatography (1:2 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2215a032e5f9454f83cc5b8245d8b56f
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094780B1

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