[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13][C:14](=[CH2:17])[CH2:15][NH2:16].C(O)(=O)C(O)=O.[F:24][C:25]([F:38])([F:37])[C:26]1[CH:36]=[CH:35][C:29]([O:30]C2CNC2)=[CH:28][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:17][C:14](=[CH2:13])[CH2:15][NH:16][C:1]([N:8]1[CH2:9][CH:11]([O:30][C:29]2[CH:35]=[CH:36][C:26]([C:25]([F:24])([F:37])[F:38])=[CH:27][CH:28]=2)[CH2:12]1)=[O:2]A stirred solution of 3.6 g (0.022 mole) of 1,1'-carbonyldiimidazole in 75 ml of methylene chloride under nitrogen was treated with 1.6 g (0.022 mole) of 2-methyl-2-propenylamine (added via a syringe and needle through a septum placed in one neck of the reaction flask). After stirring for 1 hr, 6.2 g (0.02 mole) of 3-[4-(trifluoromethyl)phenoxy]azetidine oxalate was added all at once followed in 30 min with 5 ml of triethylamine and stirring was continued for 3 hr. The reaction mixture was washed with water (2×25 ml), dried over magnesium sulfate and concentrated in vacuo. The oily residue solidified on standing and was recrystallized from isopropyl ether to yield 3.7 g (58.9%) of fine white crystals, m.p. 101°-102° C.
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