Water → 2-(4-(8-Bromo-2-oxo-3-(2-propylpentanoyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

HRID 476189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 476189
[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[NH:12][C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1.[C:27]([O-:30])(=O)[CH3:28].[Na+].O>C(OC(=O)C(CCC)CCC)(=O)C(CCC)CCC>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([C:27](=[O:30])[CH:28]([CH2:9][CH2:4][CH3:5])[CH2:3][CH2:2][CH3:11])[C:13](=[O:26])[N:14]([C:15]4[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:25])[C:22]#[N:23])=[CH:17][CH:16]=4)[C:5]=3[C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 517045Sodium AcetateHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Produkt 1

HCID 498536872-(4-(8-Bromo-2-oxo-3-(2-propylpentanoyl)-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 109236242-Propylpentanoyl 2-propylpentanoateLösungsmittel

Versuchsvorschrift

A mixture of 2-(4-(8-Bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 25 mg, 0.06 mmol) and sodium acetate (5 mg, 0.06 mmol) was heated at 110-120° C. in valproic anhydride (1 ml) for four hours. Reaction mixture was cooled to RT. Water was added and extracted with ethyl acetate. Ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 12 mg (38%); 1H NMR (CDCl3, 300 MHz): δ 9.849 (s, 1H), 7.98-8.01 (d, 1H, J=9 Hz), 7.78-7.81 (d, 2H, J=8.7 Hz), 7.63-7.67 (dd, 1H, J=9, 2.1 Hz), 7.54-7.57 (d, 2H, J=8.1 Hz), 7.02-7.03 (d, 1H, J=1.8 Hz), 2.38 (m, 1H), 1.84 (s, 6H), 1.67 (m, 4H), 1.49 (m, 4H), 0.9 (m, 6H); MS: m/z 533 (M+).

Aufarbeitung

  1. customReaction mixture
  2. extractionextracted with ethyl acetate
  3. washEthyl acetate layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-efada919a2f44e88b7442bcd28c2e171
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637670B2

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