[C:1]([C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:16])[C:13](O)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:23]([NH2:25])[CH3:24].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(#N)C>[C:1]([C:5]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:16])[C:13]([NH:25][CH2:23][CH3:24])=[O:14])[CH2:11]1)([CH3:2])([CH3:3])[CH3:4]To a stirred solution of [3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl](oxo)acetic acid (0.27 g, 0.93 mmol) and ethylamine hydrochloride (89 mg, 1.1 mmol) in acetonitrile (20.0 mL) were added EDCI (0.21 g, 1.1 mmol) and HOBt (0.17 g, 1.1 mmol) at room temperature. After 16 h the reaction mixture was concentrated under reduced pressure, the resulting residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with 10% sodium bicarbonate, saturated sodium chloride, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 66:34 to 34:66 hexane/ethyl acetate) to provide 2-[3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl]-N-ethyl-2-oxoacetamide (0.14 g, 48%) as a white powder.
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