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Diisopropylethylamine → N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamine

HRID 563852
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 563852
Cl[C:2]1[N:7]=[C:6]([NH:8][N:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)[N:5]=[C:4]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[NH2:43][CH2:44][C:45]1[CH:46]=[N:47][C:48]([Cl:51])=[CH:49][CH:50]=1>O1CCOCC1>[Cl:51][C:48]1[N:47]=[CH:46][C:45]([CH2:44][NH:43][C:2]2[N:3]=[C:4]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([F:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=3)[N:5]=[C:6]([NH:8][N:9]=[CH:10][C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][CH:12]=3)[N:7]=2)=[CH:50][CH:49]=1
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Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 70209275-(Aminomethyl)-2-chloropyridineHCID 76550911(4-Chloro-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine

Produkt 1

HCID 74437664N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamineAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

{4-Chloro-6-[N′-(4-trifluoromethoxybenzylidene)hydrazino]-1,3,5-triazin-2-yl}-(4-fluoro-3-trifluoromethylphenyl)amine (XXI) (2.54 g, 5.14 mmol) was dissolved in dioxane (25 mL). To this solution was added diisopropylethylamine (1.8 mL, 10.3 mL) followed by 3-aminomethyl-6-chloropyridine (0.52 mL, 5.17 mmol). The reaction was allowed to stir overnight at room temperature. The solvent was removed under vacuum and the residue dissolved in ethyl ether (40 mL). This solution was rinsed with brine, dried over magnesium sulfate, filtered and concentrated to give a dark yellow oil which was purified by column chromatography (silica, gel, hexane/EtOAc), to afford desired product 2 (0.93 g, 32% yield).

Aufarbeitung

  1. customThe solvent was removed under vacuum
  2. dissolutionthe residue dissolved in ethyl ether (40 mL)
  3. washThis solution was rinsed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a dark yellow oil which
  8. customwas purified by column chromatography (silica, gel, hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b7f9e76a6a6049c982c85dfdc54bf337
Quelldatensatz
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08067588B2

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