Sodium Bicarbonate → (3-(4-((4-Hydroxy-4-methylazepan-1-yl)methyl)phenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone

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Reaction Steps

Intermediate 55A (0.10 g, 0.26 mmol), 4-methylazepan-4-ol hydrochloride (0.057 g, 0.34 mmol, see Helvetica Chimica Acta, 45, 1823-32, (1962)) and TEA (0.146 mL, 1.05 mmol) were mixed in dichloromethane (4 mL). The mixture was stirred at RT for 1 h and then sodium triacetoxyhydroborate (0.112 g, 0.53 mmol) was added and the mixture was stirred at RT overnight. Aqueous NaHCO3 (sat., 3 mL) and dichloromethane (3 mL) were added and the mixture was filtered through a phase separator and the solvent was removed by evaporation. The product was purified by preparative reverse-phase HPLC at pH 10 to give 83 mg (64%). 1H NMR (600 MHz, DMSO) δ 1.11 (s, 3H), 1.35-1.8 (m, 7H), 2.31-2.65 (m, 3H), 3.51 (s, 2H), 3.88 (s, 3H), 4.07-4.12 (m, 1H), 4.51-4.66 (m, 2H), 5.06-5.18 (m, 2H), 6.85 (d, 2H), 7.16-7.3 (m, 4H), 8-8.06 (m, 2H), LC-purity: 92%.

Provenance & Evidence