C(=O)([O-])O.[Na+].[F:6][C:7]1[CH:8]=[C:9]([NH2:19])[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[N:16][C:15]([CH3:18])=[N:14]1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>C1COCC1>[CH2:24]([O:23][C:21](=[O:22])[NH:19][C:9]1[CH:10]=[CH:11][C:12]([N:13]2[CH:17]=[N:16][C:15]([CH3:18])=[N:14]2)=[C:7]([F:6])[CH:8]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1Saturated aqueous sodium hydrogencarbonate solution (375 ml) was added to a solution of 3-fluoro-4-(3-methyl-1,2,4-triazol-1-yl)phenylamine (Intermediate 27) (50.8 g, 0.265 mol) in THF (1 1). The mixture was cooled to −20° C. and benzyl chloroformate (48 ml, 0.336 mol) was added. The reaction mixture was stirred under N2, allowed to warm to room temperature and stirred for 2 days. The mixture was concentrated to approximately half the volume and diluted with ethyl acetate (1 l). The organic layer was separated and washed with water (2×), brine (2×), dried over sodium sulfate and concentrated in vacuo. Recrystallisation from ethyl acetate/hexanes (300 ml/200 ml) gave the title compound (73.0 g), m.p. 152.6-154.9° C.
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