Nitrogen → HCID 71253240, Verbindung

HRID 571086

Reaktionsgleichung

Reaktionsgleichung von HRID 571086
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=1.[C:12]([C:16]1[CH:20]=[C:19]([NH2:21])[NH:18][N:17]=1)([CH3:15])([CH3:14])[CH3:13].CN[C@@H]1CCCC[C@H]1NC.C(=O)([O-])[O-].[K+].[K+].N#N.CCCC(C)C>C1(C)C=CC=CC=1.CCOCC.[Cu]I>[C:12]([C:16]1[CH:20]=[C:19]([NH2:21])[N:18]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([O:10][CH3:11])[CH:3]=2)[N:17]=1)([CH3:15])([CH3:14])[CH3:13]

Komponenten

10

Edukt 6

HCID 947NitrogenHCID 78922-MethylpentaneHCID 11430Potassium CarbonateHCID 2303074-Iodo-1,2-dimethoxybenzeneHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 178441179HCID 178441179, Verbindung

Produkt 1

HCID 71253240HCID 71253240, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 4-iodo-1,2-dimethoxybenzene (1.10 g, 4.17 mmol) in anhydrous toluene (5.0 mL) was added 3-tert-butyl-1H-pyrazol-5-amine (638 mg, 4.58 mmol) followed by (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (130 μL, 0.83 mmol) and potassium carbonate (1.15 g, 8.3 mmol). The mixture was purged with N2, copper(I) iodide (40 mg, 0.21 mmol) was added and the reaction mixture was heated at reflux under N2 for 16 hr. The resulting mixture was cooled to RT and was partitioned between EtOAc (100 mL) and water (150 mL). The organic layer was separated and was washed with aq. citric acid solution (10% w/v, 50 mL) followed by brine (50 mL) and then dried and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 0-70%, gradient elution). The impure product so obtained was dissolved in ether (1.0 mL), isohexane (10 mL) was added and the resulting precipitate was collected by filtration to afford the title compound, Intermediate A19, as a purple solid (364 mg, 31%); Rt 3.55 min (Method 1); m/z 276 (M+H)+ (ES+).

Aufarbeitung

  1. additionwas added
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux under N2 for 16 hr
  4. customwas partitioned between EtOAc (100 mL) and water (150 mL)
  5. customThe organic layer was separated
  6. washwas washed with aq. citric acid solution (10% w/v, 50 mL)
  7. customdried
  8. customevaporated in vacuo
  9. customThe residue was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 0-70%, gradient elution)
  10. customThe impure product so obtained
  11. filtrationthe resulting precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-d00e67e6c0064cadbaed9e1c1d69663e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024041B2

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