Triethylamine → (+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide

HRID 2307466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307466
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([OH:11])=O.[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:16]=[C:17]([CH:21]([NH2:23])[CH3:22])[CH:18]=[CH:19][CH:20]=1.CCN=C=NCCCN(C)C.Cl.C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][C:9]([NH:23][CH:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][C:13]([F:12])([F:24])[F:25])[CH:16]=1)[CH3:22])=[O:11]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 2478243-(2-Pyridyl)acrylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 226055421-[3-(Trifluoromethoxy)phenyl]ethan-1-amine

Produkt 1

HCID 69919610(+/-)-3-Pyridin-2-yl-N-[1-(3-trifluoromethoxyphenyl)ethyl]acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(pyridin-2-yl)acrylic acid, Preparation 16 (50 mg) in CH2Cl2 (2 mL) at room temperature were added (±)-1-(3-trifluoromethoxy phenyl)ethylamine, Preparation 15 (76 mg), EDC hydrochloride (129 mg), DMAP (41 mg), and triethylamine (0.2 mL), and the resulting solution was stirred at room temperature for 12 hours. The crude product was purified by silica gel chromatography eluting with ethyl acetate to provide the title compound as the racemate (96 mg). This racemate was separated by HPLC using AD column eluting with hexanes/ethanol (9:1) to give the title compound as an enantiomer of undetermined chirality.

Aufarbeitung

  1. additionwere added
  2. customThe crude product was purified by silica gel chromatography
  3. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ab90da8c41264b2190e2bd26b776faf4
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06831080B2

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