Diisopropylethylamine → (4-(6-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanone

HRID 445919

Reaktionsgleichung

Reaktionsgleichung von HRID 445919
Cl[C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])[N:5]=[N:6][C:7]=1[NH2:8].[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])=[CH:22][CH:21]=1.C(N(CC)C(C)C)(C)C>O1CCOCC1>[NH2:8][C:7]1[N:6]=[N:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=2[CH3:18])=[N:3][C:2]=1[NH:19][C:20]1[CH:21]=[CH:22][C:23]([C:26]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)=[O:27])=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 5778154-(Morpholine-4-carbonyl)anilineHCID 582795485-Chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine

Produkt 1

HCID 58279511(4-(6-Amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanoneAusbeute 33,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of 5-chloro-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-6-amine (1.05 g, 3.95 mmol), (4-aminophenyl)(morpholino)methanone (1.630 g, 7.90 mmol), and N,N-diisopropylethylamine (1.243 mL, 7.11 mmol) in 1,4-dioxane (60 mL) was heated at reflux for 2 days. The volatiles were removed under vacuum. To the residue was added water (60 mL). The precipitating material was collected by suction filtration. The filter cake was purified by ISCO (120 g silica gel, solid loading, 3-8% MeOH/CH2Cl2) to provide the desired product, (4-(6-amino-3-(2-methyl-3-nitrophenyl)-1,2,4-triazin-5-ylamino)phenyl)(morpholino)methanone (0.595 g, 1.339 mmol, 33.9% yield), as a yellow solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 2 days
  3. customThe volatiles were removed under vacuum
  4. additionTo the residue was added water (60 mL)
  5. filtrationThe precipitating material was collected by suction filtration
  6. customThe filter cake was purified by ISCO (120 g silica gel, solid loading, 3-8% MeOH/CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-c5739192b8854b41a2239b479b0afb0b
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476430B2

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