Reaktion #1122409

Reaktionsgleichung

Intermediate 59E

1-(4-(Azetidin-3-ylthio)benzyl)pyrrolidine

ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate

→

59

Ausbeute 24.0%

(5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl)(3-(4-(pyrrolidin-1-ylmethyl)phenylthio)azetidin-1-yl)methanone

Ausbeute 24.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product was purified by flash-chromatography
2. 2
   SonstigeThe product crystallised when
3. 3
   workup.ADDITIONadding ether
4. 4
   Sonstigethe solid was dried in vacuo

Vorschrift

Intermediate 59E (0.37 g, 1.5 mmol) and ethyl 5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate (0.48 g, 1.9 mmol) were mixed and heated to 120° C. for 2 h using an oil-bath. The product was purified by flash-chromatography using 1-5% methanol/DCM where the methanol contained ammonia (2M). The product crystallised when adding ether and the solid was dried in vacuo. There was obtained 0.16 g (24%) of 59 as a solid. 1H NMR (500 MHz, CDCl3): δ 1.81 (m, 4H), 2.51 (m, 4H), 3.62 (m, 2H), 3.89 (s, 3H), 4.18 (m, 2H), 4.63 (m, 2H), 5.11 (m, 1H), 7.02 (d, 2H), 7.27 (m, 4H), 8.09 (d, 2H), MS (APCI+) m/z 451 [M+H]+, LC purity: 97%.

Quelle