Ethanamine, 2,2,2-trifluoro- → 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifiuoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifiuoroethyl) benzoic acid amide

HRID 452500

Reaktionsgleichung

Reaktionsgleichung von HRID 452500
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[F:28][C:29]([F:33])([F:32])[CH2:30][NH2:31].Cl.C(N(CC)CCCN=C=NCC)C>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[NH2:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:20]3[CH:21]=[C:22]([Cl:27])[CH:23]=[C:24]([Cl:26])[CH:25]=3)([C:16]([F:17])([F:18])[F:19])[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[C:4]([NH:31][CH2:30][C:29]([F:33])([F:32])[F:28])=[O:6]

Komponenten

6

Edukt 3

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochlorideHCID 66783840HCID 66783840, Verbindung

Produkt 1

HCID 866114682-amino-4-[5-(3,5-dichlorophenyl)-5-trifiuoromethyl-4,5-dihydroisoxazol-3-yl]-N-(2,2,2-trifiuoroethyl) benzoic acid amideAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

In a solution of 0.60 g of crude 2-amino-4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]benzoic acid in 6 ml of chloroform, 0.20 g of 2,2,2-trifluoroethylamine, 0.02 g of 4-(N,N-dimethylamino) pyridine and 0.33 g of 1-[3-(diethylamino)propyl]-3-ethylcarbodiimide hydrochloride were added, and stirred at room temperature for 20 hours. After the completion of the reaction, the reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that was eluted with ethyl acetate-hexane (1:4), and 0.14 g of the aimed product was obtained as pale yellow crystal.

Aufarbeitung

  1. customAfter the completion of the reaction
  2. customthe reaction mixture was subjected to purification with medium-pressure preparative liquid chromatography (Yamazen Corporation, medium pressure preparative system; YFLC-Wprep) that
  3. washwas eluted with ethyl acetate-hexane (1:4)

Quellen und Nachweise

ORD-Eintrag
ord-fa1c525400da4784947c7d0aaa783ae7
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492311B2

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