Diethylamine → N,N-Diethyl-4-{2-[(5-methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyramide

HRID 1669723Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1669723
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].C[Al](C)C.CO[C:12](=[O:34])[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([NH:26][CH2:27][C:28]1[O:29][C:30]([CH3:33])=[CH:31][CH:32]=1)=[N:21]2>O1CCOCC1>[CH2:1]([N:3]([CH2:4][CH3:5])[C:12](=[O:34])[CH2:13][CH2:14][CH2:15][C:16]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([NH:26][CH2:27][C:28]1[O:29][C:30]([CH3:33])=[CH:31][CH:32]=1)=[N:21]2)[CH3:2]

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 16682925TrimethylaluminumHCID 442181534-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester

Produkt 1

HCID 44218155N,N-Diethyl-4-{2-[(5-methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyramide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Diethylamine (89 mg, 1.22 mmol) was dissolved in 5 mL dioxane. Trimethylaluminium (2M solution in heptane, 0.61 mL, 1.22 mmol) was added and the mixture was stirred for 1 hour at room temperature. 4-{2-[(5-Methyl-furan-2-ylmethyl)-amino]-quinolin-5-yl}-butyric acid methyl ester (137 mg, 0.4 mmol) 7 mL dioxane was added and stirring was continued at 90° C. for 5 hours. The reaction mixture was quenched by addition of 0.6 mL water. The solvent was evaporated off. The residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->0:100 gradient). The title compound was obtained as a yellow oil (40 mg, 26%), MS: m/e=380.5 (M+H+).

Aufarbeitung

  1. stirringstirring
  2. waitwas continued at 90° C. for 5 hours
  3. customThe reaction mixture was quenched by addition of 0.6 mL water
  4. customThe solvent was evaporated off
  5. customThe residue was purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->0:100 gradient)

Quellen und Nachweise

ORD-Eintrag
ord-2afe320758af4a2d9c2192d861c3316b
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989628B2

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