Sodium Bicarbonate → HCID 57788017, Verbindung

HRID 249968Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249968
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([S:20]([CH3:28])(=[N:22]C(OCC)=O)=[O:21])[CH:17]=[CH:18][CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH2:30][C@H:31]([OH:33])[CH3:32].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[C:16]([S:20]([CH3:28])(=[NH:22])=[O:21])[CH:17]=[CH:18][CH:19]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:29][CH2:30][C@H:31]([OH:33])[CH3:32]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 57788013HCID 57788013, Verbindung

Produkt 1

HCID 57788017HCID 57788017, VerbindungAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

According to GWP 6, (RS)-S-(3-{[(6-bromo-4-{[(R)-2-hydroxypropyl]amino}quinazolin-7-yl)oxy]methyl}phenyl)-N-(ethoxycarbonyl)-S-methylsulphoximide (38 mg, 0.071 mmol) is dissolved in ethanol (5 mL), admixed with sodium ethoxide (17 mg, 0.25 mmol) and stirred at 60° C. for 6 hours. The reaction solution is admixed with saturated sodium bicarbonate solution and extracted with ethyl acetate. Drying of the organic phase over sodium sulphate and removal of the solvent and also chromatographic purification of the residue (silica gel, dichloromethane/methanol: 0→10% methanol) gives the desired product in 88% yield (29 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialDrying of the organic phase over sodium sulphate and removal of the solvent and also chromatographic purification of the residue (silica gel, dichloromethane/methanol: 0→10% methanol)

Quellen und Nachweise

ORD-Eintrag
ord-968bfd908dce4928945e0615740e1583
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863283B2

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