Ethyl orthoformate → 3-[(S)-(4-chlorophenyl)(3-{(1S)-2-fluoro-1-[3-fluoro-5-(1,3,4-oxadiazol-2-yl)phenyl]-2-methylpropyl}azetidin-1-yl)methyl]benzonitrile

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Reaction Steps

A solution of 41 mg (0.081 mmol) of 3-((1S)-1-{1-[(S)-(4-chlorophenyl)(3-cyanophenyl)methyl]azetidin-3-yl}-2-fluoro-2-methylpropyl)-5-fluorobenzohydrazide and 1.5 mL triethyl orthoformate in 2 mL of xylene was stirred for 3.5 at 125° C., followed by concentration to remove solvents. The residue was purified by silica gel chromatography with hexane/ethyl acetate/ammonia in MeOH to afford the title compound as a white solid; 1H-NMR(CDCl3) δ 1.23(d, 3H, J=22 Hz), 1.29(d, 3H, J=22 Hz), 2.34 (t, 1H, J=8 Hz), 2.89 (t, 1H, J=8 Hz), 2.98 (m, 1H), 3.02 (t, 1H, J=11 Hz), 3.25 (m, 1H), 3.63 (t, 1H, J =6 Hz), 4.23 (s, 1H), 7.11-7.73 (m, 11H), 8.51(s, 1H); Mass Spectrum: m/e=519 (M+1, 35Cl), 521 (M+1, 37Cl).

Provenance & Evidence