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N,N-dimethyl-m-phenylenediamine → 6-((2-(3-(dimethylamino)phenylamino)pyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16238
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 16238
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:23])[C:9]2[CH:22]=[CH:21][C:12]3[C:13]([C:17]([NH:19][CH3:20])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:24][N:25]([CH3:33])[C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][CH:32]=1)[NH2:29]>CN(C=O)C>[CH3:24][N:25]([CH3:33])[C:26]1[CH:27]=[C:28]([NH:29][C:2]2[N:7]=[C:6]([N:8]([CH3:23])[C:9]3[CH:22]=[CH:21][C:12]4[C:13]([C:17]([NH:19][CH3:20])=[O:18])=[C:14]([CH3:16])[O:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:30]=[CH:31][CH:32]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 76084N,N-dimethyl-m-phenylenediamineHCID 592247476-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide

Produkt 1

HCID 446344836-((2-(3-(dimethylamino)phenylamino)pyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide (0.1 mmol) and 3-dimethylaminoaniline (0.1 mmol) were dissolved in 0.5 ml DMF. To this was added p-TsOH monohydrate (0.2 mmol). The reaction mixture was stirred at 60° C. for 5 hours, and subjected to extraction with EtOAc. Then water was added and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated. The resulting residue was purified by column chromatography to provide the title product in a yield of 78%.

Aufarbeitung

  1. extractionsubjected to extraction with EtOAc
  2. additionThen water was added
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washThe organic layer was washed with water and brine sequentially
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6319f4d90ee340cbb34c2715c3d9de01
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07737157B2

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