Ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate → (3-(4-((Dimethylamino)methyl)-3-methylphenoxy)azetidin-1-yl)(5-phenyl-1,3,4-oxadiazol-2-yl)methanone
Reaktionsgleichung
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]([CH3:15])[CH3:14])=[C:8]([CH3:16])[CH:7]=2)[CH2:2]1.[C:17]1([C:23]2[O:27][C:26]([C:28](OCC)=[O:29])=[N:25][N:24]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH3:14][N:13]([CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH:3]2[CH2:2][N:1]([C:28]([C:26]3[O:27][C:23]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[N:24][N:25]=3)=[O:29])[CH2:4]2)=[CH:7][C:8]=1[CH3:16])[CH3:15]Komponenten
3
Reaktionsbedingungen
- Temperatur
- 120 °C
Versuchsvorschrift
Intermediate 20C (0.16 g, 0.73 mmol) and ethyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate (0.17 g, 0.80 mmol) were mixed together in a microwave vial. The vial was sealed and the mixture was then stirred at 120° C. for 2 hours using an oil bath. The mixture was cooled to room temperature. The product was purified by column chromatography eluting with DCM and MeOH (saturated with ammonia)/DCM (gradient, 0.5-2%). The solvent was removed by evaporation and the semi solid residue was triturated with Et2O. There was obtained 0.27 g (93%) of the product as a crystalline solid m.p. 135° C. 1H NMR (600 MHz, CDCl3): δ 2.21 (s, 6H), 2.34 (s, 3H), 3.31 (s, 2H), 4.28-4.35 (m, 1H), 4.59-4.67 (m, 1H), 4.70-4.78 (m, 1H), 5.01-5.15 (m, 2H), 6.54 (d, 1H), 6.60 (s, 1H), 7.15 (d, 1H), 7.49-7.62 (m, 3H), 8.16 (d, 2H), MS (APCI+) m/z 393 [M+H]+, LC purity: 99%.