Triethylamine → N-{2-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}-2-methylpropanamide

HRID 1245924Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1245924
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[NH2:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][N:13]1[C:21]2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=[C:17]([NH2:24])[C:16]=2[N:15]=[C:14]1[CH3:25].C(N(CC)CC)C>C(Cl)(Cl)Cl>[NH2:24][C:17]1[C:16]2[N:15]=[C:14]([CH3:25])[N:13]([CH2:12][CH2:11][O:10][CH2:9][CH2:8][NH:7][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[C:21]=2[C:20]([CH3:22])=[C:19]([CH3:23])[N:18]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 219130531-[2-(2-aminoethoxy)ethyl]-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

Produkt 1

HCID 21913758N-{2-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}-2-methylpropanamideAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

Under a nitrogen atmosphere, isobutyryl chloride (330 μL, 3.15 mmol) was added to a solution of 1-[2-(2-aminoethoxy)ethyl]-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine (0.757 g, 2.875 mmol) in chloroform (11 mL) and triethylamine (520 μL, 3.78 mmol). The reaction mixture was stirred at ambient temperature for about 3 hours; then it was diluted with chloroform (20 mL) and washed with saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography (10 g of silica gel eluting with 2% methanol in chloroform containing 0.5% triethylamine) to provide 0.3486 g of N-{2-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethoxy]ethyl}-2-methylpropanamide as a solid, m.p. 179.5–182° C.

Aufarbeitung

  1. washwashed with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography (10 g of silica gel eluting with 2% methanol in chloroform containing 0.5% triethylamine)

Quellen und Nachweise

ORD-Eintrag
ord-b97c16fdf94b42369f3e930d34b656ff
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07125890B2

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