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

HRID 476166

Reaktionsgleichung

Reaktionsgleichung von HRID 476166
[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:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:36]=1[S:44](Cl)(=[O:46])=[O:45].O>ClCCl>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([S:44]([C:36]4[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:35]=4[CH3:34])(=[O:45])=[O:46])[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 8457o-Toluenesulfonyl chloride, 5-nitro-HCID 8471TriethylamineHCID 426095694-(8-Bromo-2,3-dihydro-2-oxo-1H-imidazo(4,5-c)quinolin-1-yl)-alpha,alpha-dimethylbenzeneacetonitrile2×

Produkt 1

HCID 668971492-(4-(8-Bromo-3-(2-methyl-5-nitrophenylsulfonyl)-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, 0.24 mmol) in dichloromethane (6 ml) was added 2-methyl-5-nitrobenzene-1-sulfonyl chloride (53 mg, 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 dried over sodium sulfate and crude product was purified by column chromatography (silica gel, 2% acetone in chloroform) to obtain the title compound.

Aufarbeitung

  1. customwas separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialThe combined organic layer was dried over sodium sulfate and crude product
  4. customwas purified by column chromatography (silica gel, 2% acetone in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-583fdc6fb634442cb6aa1a8f5a4ddba2
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637670B2

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