[Cl:1][C:2]1[N+:7]([O-:8])=[C:6]([CH2:9][C:10]([O:12]C2C=CC([N+]([O-])=O)=CC=2)=O)[C:5]([C:22]#[N:23])=[CH:4][CH:3]=1.[C:24]([O:28][C:29](=[O:42])[NH:30][C:31]1[C:35]2[CH:36]=[C:37]([CH2:40][NH2:41])[CH:38]=[CH:39][C:34]=2[O:33][N:32]=1)([CH3:27])([CH3:26])[CH3:25].CO>CCOC(C)=O.CCCCCC>[C:22]([C:5]1[C:6]([CH2:9][C:10]([NH:41][CH2:40][C:37]2[CH:38]=[CH:39][C:34]3[O:33][N:32]=[C:31]([NH:30][C:29]([O:28][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:42])[C:35]=3[CH:36]=2)=[O:12])=[N+:7]([O-:8])[C:2]([Cl:1])=[CH:3][CH:4]=1)#[N:23]A mixture of 6-chloro-3-cyano-2-(4-nitro-phenoxycarbonylmethyl)-pyridine 1-oxide (83.6 mg, 0.25 mmol), as prepared in Example 6f, and (5-aminomethyl-benzo[d]isoxazol-3-yl)-carbamic acid tert-butyl ester (78.8 mg, 0.3 mmol) in CDCl3 (3 mL) was stirred in an ice-water bath which was allowed to rise to rt overnight. A lot of precipitate formed. TLC showed the disappearance of 6-chloro-3-cyano-2-(4-nitro-phenoxycarbonylmethyl)-pyridine 1-oxide. A small amount of methanol was added to dissolve the solid. The solution was applied onto a prep TLC (2 mm, 20×20 cm) and developed with EtOAc/Hexane (4:1). A white solid was obtained (103 mg). LC/MS (ESI) (M+H+ 458.1)
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