Diisopropylethylamine → HCID 58248008, Verbindung

HRID 339133

Reaktionsgleichung

Reaktionsgleichung von HRID 339133
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18](O)=[O:19])=[CH:12][C:11]=1[C:21]([F:24])([F:23])[F:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C=C(O)C2N=NNC=2C=1.Cl.C(N=C=NCCCN(C)C)C.CCN(C(C)C)C(C)C.[F:57][C:58]([F:72])([F:71])[CH:59]([C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([C:67]([F:70])([F:69])[F:68])[CH:62]=1)[NH2:60]>ClCCl>[O:19]=[C:18]([NH:60][CH:59]([C:61]1[CH:66]=[CH:65][CH:64]=[C:63]([C:67]([F:68])([F:69])[F:70])[CH:62]=1)[C:58]([F:71])([F:72])[F:57])/[CH:17]=[CH:16]/[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:11]([C:21]([F:22])([F:23])[F:24])[CH:12]=1

Komponenten

7

Edukt 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 438251722,2,2-Trifluoro-1-(3-(trifluoromethyl)phenyl)ethanamineHCID 58248002HCID 58248002, VerbindungHCID 178516184HCID 178516184, Verbindung

Produkt 1

HCID 58248008HCID 58248008, VerbindungAusbeute 130,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 980 mg (1 eq, 2.84 mmol) of (2E)-3-[4-{[(tert-butoxycarbonyl)amino]methyl}-3-(trifluoromethyl)phenyl]acrylic acid in 10 ml of dichloromethane were added 481 mg (1 eq, 2.84 mmol) of 6-chlorohydroxybenzotriazole and 707 mg (1.3 eq, 3.70 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC) and 733 mg (2 eq, 5.68 mmol, 989 μl) of Huenig's base. The reaction mixture was stirred at room temperature for 20 min. Then 1.04 g (1.5 eq, 4.26 mmol) of 2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethanamine as a solution in 1 ml of CH2Cl2 were added, and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure and partitioned between saturated Na2CO3 solution and ethyl acetate. After drying and concentrating the solvent, 2.108 g of tert-butyl {4-[(1E)-3-oxo-3-({2,2,2-trifluoro-1-[3-(trifluoromethyl)phenyl]ethyl}amino)prop-1-en-1-yl]-2-(trifluoromethyl)benzyl}carbamate were obtained as an oil, which was converted in the next step without further purification.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompartitioned between saturated Na2CO3 solution and ethyl acetate
  4. customAfter drying
  5. concentrationconcentrating the solvent

Quellen und Nachweise

ORD-Eintrag
ord-55855fea772f40799346b45cbe51438d
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889878B2

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