Dimethylformamide → HCID 22674164, Verbindung

HRID 1173139Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173139
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[Br:12].Cl[C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][N:15]=1.CN(C)C=O.[CH3:29][S-:30].[Na+]>[Cl-].[Na+].O.N1C=CC=CC=1>[Br:12][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([NH:1][S:20]([C:17]1[CH:18]=[CH:19][C:14]([S:30][CH3:29])=[N:15][CH:16]=1)(=[O:22])=[O:21])=[CH:11]2

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 4378561Sodium methanethiolateHCID 226741618-Bromoquinolin-3-amine

Produkt 1

HCID 22674164HCID 22674164, VerbindungAusbeute 27 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

197 mg (0.556 mmol) of white crystals were obtained using 100 mg (0.56 mmol, Production Example 5b) of 3-amino-8-bromoquinoline and 142 mg (0.67 mmol) of 2-chloro-5-pyridinesulfonyl chloride in the same manner as in Synthetic Example 1b. Dimethylformamide (1 ml), pyridine (1 ml) and 111 mg (1.6 mmol) of sodium thiomethoxide were added to 60 mg (0.17 mmol) of the crystals, followed by stirring at room temperature for 3 hours. Brine was added to the reaction solution, followed by extracting with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated, to give the residue. The residue was purified by silica gel chromatography, to give 62 mg of the title compound.

Aufarbeitung

  1. extractionby extracting with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customto give the residue
  5. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-9cc8a4e4094943219b9ad84b901a812f
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834049B2

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