Triethylamine → 4-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-piperidine-1-carboxylic acid benzyl ester

HRID 2244824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2244824
[NH2:1][C:2]1[C:3](=[O:14])[N:4]([CH3:13])[C:5]2[C:10]([C:11]=1[NH2:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.CCN(CC)CC.[CH2:22]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([C:38](Cl)=O)[CH2:34][CH2:33]1)=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][C:30]([N:32]1[CH2:37][CH2:36][CH:35]([C:38]2[NH:1][C:2]3[C:3](=[O:14])[N:4]([CH3:13])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=4[C:11]=3[N:12]=2)[CH2:34][CH2:33]1)=[O:31])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylateHCID 451232943,4-Diamino-1-methylquinolin-2(1H)-one

Produkt 1

HCID 587884444-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-piperidine-1-carboxylic acid benzyl esterAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3,4-diamino-1-methyl-1H-quinolin-2-one (0.60 g, 1.59 mmol) in CH2Cl2 (10 mL) were added Et3N (0.177 g, 1.74 mmol) and 4-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (0.45 g, 1.60 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1.5 h, and then excess acid chloride was quenched by addition of MeOH. The mixture was concentrated in vacuo, and the amide intermediate was taken up in 5 mL of HOAc and heated at reflux for 7 h. After cooling to room temperature, the solvent was evaporated under reduced pressure. The cyclized product was purified by flash chromatography, to give 4-(5-methyl-4-oxo-4,5-dihydro-3H-imidazo[4,5-c]quinolin-2-yl)-piperidine-1-carboxylic acid benzyl ester (0.12 g, 18% yield). 1H-NMR (DMSO): δ 8.08 (m, 1H), 7.60 (m, 1H), 7.43 (m, 1H), 7.32 (m, 6H), 5.02 (s, 2H), 3.91 (m, 2H), 3.34 (s, 3H), 2.81 (m, 3H), 1.78 (m, 2H), 1.39 (m, 2H). MS: calculated for C24H24N4O3+H 417.2; found: 417.4.

Aufarbeitung

  1. customexcess acid chloride was quenched by addition of MeOH
  2. concentrationThe mixture was concentrated in vacuo
  3. temperatureheated
  4. temperatureat reflux for 7 h
  5. temperatureAfter cooling to room temperature
  6. customthe solvent was evaporated under reduced pressure
  7. customThe cyclized product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21401eccdb68486cb7d3f12535fff39d
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07678909B1

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