1,2-Diaminocyclohexane, trans- → HCID 58945868, Verbindung

HRID 2267151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2267151
P([O-])([O-])([O-])=O.[K+].[K+].[K+].N[C@@H]1CCCC[C@H]1N.[Cl:17][C:18]1[C:23]([N:24]2[C:28]([CH3:29])=[C:27](I)[N:26]=[N:25]2)=[CH:22][CH:21]=[CH:20][N:19]=1.[C:31]([O:35][C:36]([N:38]1[CH2:43][CH2:42][NH:41][C:40](=O)[CH2:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>O1CCOCC1.[Cu]I.O>[Cl:17][C:18]1[C:23]([N:24]2[C:28]([CH3:29])=[C:27]([N:41]3[CH2:40][CH2:39][N:38]([C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[CH2:43][CH2:42]3)[N:26]=[N:25]2)=[CH:22][CH:21]=[CH:20][N:19]=1

Komponenten

8

Edukt 4

HCID 438061,2-Diaminocyclohexane, trans-HCID 62657Potassium Phosphate, TribasicHCID 3157178Tert-butyl 3-oxopiperazine-1-carboxylateHCID 498535132-Chloro-3-(4-iodo-5-methyl-1H-1,2,3-triazol-1-yl)pyridine

Produkt 1

HCID 58945868HCID 58945868, VerbindungAusbeute 9,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a nitrogen atmosphere, 200 mg of tripotassium phosphate, 5 mg of copper(I) iodide and 0.1 ml of trans-1,2-diaminocyclohexane were successively added to a solution of 60 mg of 1-(2-chloropyridin-3-yl)-5-methyl-4-iodo-1H-[1,2,3]triazole and 50 mg of 4-(tert-butyloxycarbonyl)piperazin-2-one in 2 ml of dioxane and the mixture was stirred for one night at 90° C. After addition of water, the product was extracted with ethyl acetate and the organic layer washed with water and dried over sodium sulfate. A borane methyl sulfide complex (0.1 ml) was added to the residue after evaporation of the solvent in vacuo and the mixture was stirred at room temperature for 1 hour. After addition of pyridine, the residue prepared by evaporation in vacuo was purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=3:1) to give 7 mg of the title compound as a white solid.

Aufarbeitung

  1. extractionthe product was extracted with ethyl acetate
  2. washthe organic layer washed with water
  3. dry with materialdried over sodium sulfate
  4. additionA borane methyl sulfide complex (0.1 ml) was added to the residue
  5. customafter evaporation of the solvent in vacuo
  6. stirringthe mixture was stirred at room temperature for 1 hour
  7. additionAfter addition of pyridine
  8. customthe residue prepared by evaporation in vacuo
  9. customwas purified by a preparative thin-layer silica gel chromatography (hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-71213a13234f4e48b51894323fc7c362
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07858800B2

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