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Reagents and conditions: (a) Trichloroacetic anhydride, HOBt, toluene, 120 °C, 2.5 h; (b) 57, MeOH, RT, 10 days; (c) TFA, RT, 0.5 h; (d) 47, 1-butanol, DIPEA, 150 °C, 15 min in microwave; (e) 6 N HCl, methanol, 60 °C, 1 h; (f) NaOAc, cyanogen bromide, methanol, 0 °C to RT, 5 h; (g) HONH2 HCl, ethanol, Na2CO3, 85 °C, 3 h; (h) 4-methylbenzoic acid, EDC, HOBt, DCM, RT, 14 h; (i) NaOAc, ethanol, water, 85 °C, 3 h; (j) thiosemicarbazide; (k) CuCl, NaNO2, HCl.
