Diisopropylethylamine → HCID 86616129, Verbindung

HRID 545271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 545271
C(N(CC)C(C)C)(C)C.Cl[C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=1.[CH2:23]([N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH2:27])[CH:24]=[CH2:25]>O.O1CCCC1.C1(C)C=CC=CC=1>[CH2:23]([N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:27][C:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][N:14]=[C:13]([Cl:22])[CH:12]=1)[CH:24]=[CH2:25]

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylateHCID 10535205tert-Butyl 1-allylhydrazinecarboxylate

Produkt 1

HCID 86616129HCID 86616129, VerbindungAusbeute 18,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

7.0 mL of N,N-diisopropylethylamine was added to tetrahydrofuran (70 mL) solution of 4.40 g of ethyl 4,6-dichloronicotinate and 3.44 g of tert-butyl 1-allylhydrazinecarboxylate obtained in Production Example 1-1, and stirred overnight at 70° C. 30 mL of toluene was added to the reaction liquid, and tetrahydrofuran was evaporated away. This was stirred at 120° C. for 6 hours, and then heated overnight under reflux. The reaction liquid was restored to room temperature, water was added thereto, and extracted with ethyl acetate. This was washed with saturated saline water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (hexane/ethyl acetate=16/1 to 12/1) to obtain 1.29 g of the entitled compound as a colorless oily substance.

Aufarbeitung

  1. customobtained in Production Example 1-1
  2. customwas evaporated away
  3. stirringThis was stirred at 120° C. for 6 hours
  4. temperatureheated overnight
  5. temperatureunder reflux
  6. customThe reaction liquid
  7. customwas restored to room temperature
  8. extractionextracted with ethyl acetate
  9. washThis was washed with saturated saline water
  10. dry with materialdried with anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate=16/1 to 12/1)

Quellen und Nachweise

ORD-Eintrag
ord-7fd2c4b758744beb87a1e6f30c617123
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935708B2

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