Potassium Carbonate → [5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yloxy]-acetic acid methyl ester

HRID 33811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 33811
N[C:2]1[CH:15]=[C:14]2[C:5]([S:6][C:7]3[C:8]([C:16]4[O:17][C:18]([N:23]5[CH2:28][CH2:27][O:26][CH2:25][CH2:24]5)=[CH:19][C:20](=[O:22])[CH:21]=4)=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:13]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-:30].[K+].[K+].[CH3:35][O:36][C:37](=[O:40])[CH2:38]Br>CN(C=O)C>[CH3:35][O:36][C:37](=[O:40])[CH2:38][O:30][C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][C:8]=3[C:16]3[O:17][C:18]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[CH:19][C:20](=[O:22])[CH:21]=3)[CH2:13][C:14]=2[CH:15]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 221394022-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

Produkt 1

HCID 86596854[5-(6-Morpholin-4-yl-4-oxo-4H-pyran-2-yl)-9H-thioxanthen-2-yloxy]-acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(7-Amino-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one (1.01 g, 2.56 mmol) in anhydrous DMF (25 ml) was added powdered potassium carbonate (716 mg, 5.18 mmol) followed by methylbromoacetate (400 μl, 4.1 mmol). The reaction was stirred at room temperature for 100 hours whereupon it was quenched by dropwise addition of water (75 ml). The mixture was extracted using EtOAc (3×30 ml). The organic extracts were then combined, dried using MgSO4, filtered and concentrated in vacuo to give the title compound as a brown oil that was used without further purification (1.02 g, 85.7%), m/z (LC-MS, ESP), RT=4.05 min, (M++1)=466

Aufarbeitung

  1. customwas quenched by dropwise addition of water (75 ml)
  2. extractionThe mixture was extracted
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-64febad9b7f94065ae4c87c895d1f4f6
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07429660B2

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