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

HRID 476168

Reaktionsgleichung

Reaktionsgleichung von HRID 476168
[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(N(CC)CC)C.[CH3:34][C:35]1[CH:36]=[C:37]([S:42](Cl)(=[O:44])=[O:43])[CH:38]=[C:39]([CH3:41])[CH:40]=1.O>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:42]([C:37]4[CH:38]=[C:39]([CH3:41])[CH:40]=[C:35]([CH3:34])[CH:36]=4)(=[O:44])=[O:43])[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

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 27362353,5-Dimethylbenzenesulfonyl chlorideHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Produkt 1

HCID 498548292-(4-(8-Bromo-3-(3,5-dimethylphenylsulfonyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-(8-bromo-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile (Intermediate 1, 50 mg, 0.12 mmol) and triethylamine (24.4 mg (0.36 mmol) in dichloromethane (6 ml) was added 3,5-dimethylbenzene-1-sulfonyl chloride (0.18 mmol) at 0° C. The reaction was stirred at RT for 3 hours. The reaction mixture was poured into cold water and organic layer was separated. The aqueous layer was extracted with dichloromethane. The combined organic layer was washed with brine dried over sodium sulfate and evaporated to dryness. The crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound. Yield: 25 mg (33.33%); 1H NMR (CDCl3, 300 MHz): δ 9.58 (s, 1H), 7.957-7.987 (d, 1H, J=9 Hz), 7.79 (s, 2H), 7.699-7.727 (d, 2H, J=8.4 Hz), 7.605-7.642 (dd, 1H, J=9 Hz, 2.1 Hz), 7.425-7.453 (d, 2H, J=8.4 Hz), 7.29 (s, 1H), 6.96 (d, 1H, J=1.8 Hz), 2.36 (s, 6H), 1.79 (s, 6H); MS: m/z 575 (M+).

Aufarbeitung

  1. customwas separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe crude product was purified by column chromatography (silica gel, 2% acetone in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-01047136130c46ec966f494d69d264ff
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637670B2

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