Pyridine, 3-(4-aminobutyl)- → (E)-5,5-bis(3-fluorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide

HRID 1110533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110533
[N+](C1C=CC(O[C:11](=[O:30])/[CH:12]=[CH:13]/[CH:14]=[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=CC=1)([O-])=O.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH2:37][CH2:38][CH2:39][CH2:40][NH2:41])[CH:32]=1>O1CCCC1>[F:29][C:25]1[CH:24]=[C:23]([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:14]/[CH:13]=[CH:12]/[C:11]([NH:41][CH2:40][CH2:39][CH2:38][CH2:37][C:33]2[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=2)=[O:30])[CH:28]=[CH:27][CH:26]=1

Komponenten

4

Edukt 2

HCID 72927Pyridine, 3-(4-aminobutyl)-HCID 14347311(E)-5,5-bis(3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester

Produkt 1

HCID 14347330(E)-5,5-bis(3-fluorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

As in Example 134, a solution of (E)-5,5-bis-(3-fluorophenyl)-2,4-pentadienoic acid 4-nitrophenyl ester (25.85 g) and 3-pyridinebutanamine (10 g) in tetrahydrofurane (100 mL) was stirred for 18 hours at room temperature and was worked up in the usual manner. The crude product was purified by HPLC (ethyl acetate) and then crystallized from ethyl acetate-hexane to afford 23.9 g of (E)-5,5-bis(3-fluorophenyl)-N-[4-(3-pyridinyl)butyl]-2,4-pentadienamide mp 103°-104° C. Anal. Calculated for C26H24F2N2O: C, 74.62; H, 5.78; F, 9.08; N, 6.69 Found: C, 74.35; H, 5.99; F, 8.93; N. 6.59.

Aufarbeitung

  1. customThe crude product was purified by HPLC (ethyl acetate)
  2. customcrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-b62898cfcf094876892fb40c7ef517b1
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04975438

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