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

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Reaction Conditions

Reaction Steps

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%.

Provenance & Evidence