Dimethylformamide → 4-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

HRID 2307989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2307989
[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1Cl.[CH3:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1N(C)C.[C:29](=O)([O-])[O-].[K+].[K+].C[N:36]([CH:38]=O)C>[Cu]>[CH3:1][O:2][C:3](=[O:18])[C:4]1[C:9]([NH:10][CH:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[CH:8][C:7]([CH3:16])=[N:6][C:5]=1[NH:36][C:38]1[C:25]([CH3:21])=[CH:26][C:27]([CH3:29])=[CH:28][C:20]=1[CH3:19]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11869N,N,2-TrimethylanilineHCID 248068762-Chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester

Produkt 1

HCID 695872624-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

A mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester, trimethylaniline, potassium carbonate, copper in DMF was heated at reflux. The mixture was quenched with ammonium chloride and stirred for 20 min, filtered through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as a solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe mixture was quenched with ammonium chloride
  4. filtrationfiltered through celite
  5. washwashed with ethyl acetate
  6. extractionThe filtrate was extracted with ethyl acetate
  7. customThe organic layer was separated
  8. customdried
  9. concentrationconcentrated to dryness
  10. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-8c360d1ba41740148e33d58c358212d7
Quelldatensatz
uspto-grants-2004_12
Patentnummer
US06833378B2

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