N,N'-Dimethylethylenediamine → HCID 70980214, Verbindung

HRID 1749080Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749080
[CH3:1][O:2][C:3]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:4]=1[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]2[NH:15][C:14](=[O:16])[CH2:13][O:12][C:11]=2[N:17]=1.I[C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1.CNCCNC.[F-].[Cs+]>CC#N.[Cu]I>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([N:15]2[C:14](=[O:16])[CH2:13][O:12][C:11]3[N:17]=[C:7]([NH:6][CH2:5][C:4]4[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:3]=4[O:2][CH3:1])[CH:8]=[CH:9][C:10]2=3)=[CH:26][CH:27]=1

Komponenten

7

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 125101-Chloro-4-iodobenzeneHCID 25953Cesium fluorideHCID 70980205HCID 70980205, Verbindung

Produkt 1

HCID 70980214HCID 70980214, VerbindungAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

6-(2,4-Dimethoxy-benzylamino)-1H-pyrido[2,3-b][1,4]oxazin-2-one (3.76 g, 11.9 mmol), 4-iodo-chlorobenzene (3.4 g, 14.3 mmol), N,N′-dimethylethylenediamine (1.27 mL, 11.9 mmol), and CsF (4.5 g, 29.7 mmol) were suspended in MeCN (100 mL) and sparged with nitrogen. CuI (238 mg, 1.19 mmol) was then added and the mixture stirred at 80° C. for 16 hours. The mixture was allowed to cool and was then concentrated in vacuo. The residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution. The EtOAc layer was then washed with saturated aqueous ammonium chloride solution, brine, dried over MgSO4, filtered and then concentrated in vacuo. The residue was purified using SiO2 chromatography (20-70% EtOAc/Petrol) to give 1-(4-chloro-phenyl)-6-(2,4-dimethoxybenzylamino)-1H-pyrido[2,3-b][1,4]oxazin-2-one (4.42 g) as a pale yellow crystalline solid. MS: [M+H]+=426.

Aufarbeitung

  1. customsparged with nitrogen
  2. temperatureto cool
  3. concentrationwas then concentrated in vacuo
  4. customThe residue was partitioned between EtOAc and aqueous potassium hydrogenphosphate solution
  5. washThe EtOAc layer was then washed with saturated aqueous ammonium chloride solution, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-440eb019f01946db917527e87d38a543
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09155743B2

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