Water → 5,6-dihydro-2-(2-phenylethyl)-6-(2-pyridinecarboxamido)-4H-imidazo[4,5,1-ij]quinoline

HRID 341842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341842
[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH2:21])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.Cl.[N:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35](Cl)=[O:36].O>ClCCl>[C:1]1([CH2:7][CH2:8][C:9]2[N:19]3[C:20]4[C:15]([CH:16]([NH:21][C:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][N:29]=5)=[O:36])[CH2:17][CH2:18]3)=[CH:14][CH:13]=[CH:12][C:11]=4[N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 135033Picolinoyl Chloride HydrochlorideHCID 158384675,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine

Produkt 1

HCID 158384705,6-dihydro-2-(2-phenylethyl)-6-(2-pyridinecarboxamido)-4H-imidazo[4,5,1-ij]quinolineAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A portion (0.4 g) of the 5,6-dihydro-2-(2-phenylethyl)-4H-imidazo[4,5,1-ij]quinolin-6-amine obtained in Step 2 of Example 17 was dissolved in anhydrous dichloromethane (5 mL); following the addition of pyridine (0.26 mL), picolinoyl chloride hydrochloride (0.28 g) was added under cooling with ice. After stirring for 4 hrs at room temperature, water (50 mL) and dichloromethane (50 mL) were added to the reaction solution and then two layers were separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: ethyl acetate) to yield the titled compound as pale brown crystals (0.31 g).

Aufarbeitung

  1. additionwas added
  2. temperatureunder cooling with ice
  3. customtwo layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-8e13087f30884f59acfc9cc869977142
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856334

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