Diisopropylethylamine → 4-[4-(4-Fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-6-methyl-1-{[2-(trifluoromethyl)thiazol-5-yl]methyl}-1,3,5-triazin-2(1H)-one

HRID 1477735

Reaktionsgleichung

Reaktionsgleichung von HRID 1477735
[CH3:1][C:2]1[N:7]([CH2:8][C:9]2[S:13][C:12]([C:14]([F:17])([F:16])[F:15])=[N:11][CH:10]=2)[C:6](=[O:18])[N:5]=[C:4](SC)[N:3]=1.Cl.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)=[CH:25][CH:24]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:34][CH2:33][N:32]([C:4]3[N:3]=[C:2]([CH3:1])[N:7]([CH2:8][C:9]4[S:13][C:12]([C:14]([F:17])([F:16])[F:15])=[N:11][CH:10]=4)[C:6](=[O:18])[N:5]=3)[CH2:31][CH:30]=2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 1977474-(4-Fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochlorideHCID 1178393126-Methyl-4-(methylthio)-1-{[2-(trifluoromethyl)thiazol-5-yl]methyl}-1,3,5-triazin-2 (1H)-one

Produkt 1

HCID 1178401374-[4-(4-Fluorophenyl)-5,6-dihydropyridin-1(2H)-yl]-6-methyl-1-{[2-(trifluoromethyl)thiazol-5-yl]methyl}-1,3,5-triazin-2(1H)-oneAusbeute 61,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a 1,4-dioxane solution (500 μL) of 6-methyl-4-(methylthio)-1-{[2-(trifluoromethyl)thiazol-5-yl]methyl}-1,3,5-triazin-2(1H)-one (38.7 mg, 0.120 mmol) synthesized in Reference Synthesis Example 374, 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine hydrochloride (30.8 mg, 0.144 mmol) and N,N-diisopropylethylamine (41.1 μL, 0.240 mmol) were added and the resultant mixture was stirred under reflux by heating for 1 day. After the completion of the reaction, the reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→0/1) to obtain the title compound (33.3 mg, yield: 61%).

Aufarbeitung

  1. additionwere added
  2. temperatureunder reflux
  3. temperatureby heating for 1 day
  4. customAfter the completion of the reaction
  5. customthe reaction solution was purified by silica gel column chromatography (hexane/ethyl acetate=1/1→0/1)

Quellen und Nachweise

ORD-Eintrag
ord-402f0ce1736b4f5a8e93b0de8ff18452
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09403798B2

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