Chloroform → 7-Hydroxy-2-(6-phenylsulfanyl-pyridin-3-yl)-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester
Reaktionsgleichung
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18](Cl)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C(N(CC)CC)C.C(Cl)(Cl)Cl.[C:34]1([SH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][C:18]([S:40][C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]Komponenten
5
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
A suspension of 2-(6-chloro-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester, example 92(c)(0.25 g, 0.75 mmol) and triethylamine (0.21 mL, 1.49 mmol) in thiophenol was heated at 100° C. overnight. 100 mL of chloroform was added. The organic solution was washed with saturated sodium bicarbonate solution and brine, dried, filtered, and concentrated. The crude product was purified by flash chromatography eluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes to produce 49.0 mg of a light yellow solid. MS: (+) m/z 410.3 (M+1).
Aufarbeitung
- washThe organic solution was washed with saturated sodium bicarbonate solution and brine
- customdried
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by flash chromatography
- washeluting from silica gel with a gradient of 0-100% ethyl acetate in hexanes
Quellen und Nachweise
- ORD-Eintrag
- ord-07c84e336c8a48abb1f3be0eef87f2e3
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07696223B2
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