Carbamate → Tert-butyl 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propylcarbamate

HRID 11359

Reaktionsgleichung

Reaktionsgleichung von HRID 11359
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[Cl:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18](Cl)[C:17]([CH3:24])=[C:16]([CH3:25])[N:15]=1.C(N(CC)CC)C.C(=O)([O-])N>CN(C)C=O>[Cl:13][C:14]1[C:19]([N+:20]([O-:22])=[O:21])=[C:18]([NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[C:17]([CH3:24])=[C:16]([CH3:25])[N:15]=1

Komponenten

6

Edukt 4

HCID 276CarbamateHCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 121091232,4-Dichloro-5,6-dimethyl-3-nitropyridine

Produkt 1

HCID 21973807Tert-butyl 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propylcarbamateAusbeute 77,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

A solution of tert-butyl 3-aminopropylcarbamate (121.39 g, 697 mmol) in N,N-dimethylformamide (200 mL) was slowly added to a solution of 2,4-dichloro-5,6-dimethyl-3-nitropyridine (110 g, 498 mmol) and triethylamine (104 mL, 746 mmol) in N,N-dimethylformamide (900 mL). After stirring at ambient temperature for 20 hours the reaction mixture was heated to 55° C. At 24 hours 0.1 equivalents of the carbamate was added. The reaction mixture was allowed to cool to ambient temperature overnight and then concentrated under reduced pressure. The residue was dissolved in ethyl acetate (3 L). The solution was divided into 3 aliquots (1 L each). Each aliquot was washed with water (2×1 L). The pH of the aqueous washes was adjusted to 10 with potassium carbonate and then they were extracted with ethyl acetate. All of the ethyl acetate layers were combined, dried over sodium sulfate and then concentrated under reduced pressure to provide 181 g of crude product. This material was recrystallized from acetonitrile to provide 138 g of tert-butyl 3-[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]propylcarbamate as a yellow solid.

Aufarbeitung

  1. temperaturewas heated to 55° C
  2. temperatureto cool to ambient temperature overnight
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate (3 L)
  5. washEach aliquot was washed with water (2×1 L)
  6. extractionthey were extracted with ethyl acetate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto provide 181 g of crude product
  10. customThis material was recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-48af6048d9f14699baeecd54e5333864
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098221B2

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