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. 2021 Oct 30;14(11):1109. doi: 10.3390/ph14111109

Figure 4.

Figure 4

Preparation of compounds 1722. Reagents and conditions: (a) tert-butyl-piperazine, K2CO3, DMSO, 80 °C, 72 h; (b) trifluoroacetic acid, CH2Cl2, rt, 24 h; (c) triethylamine, acetyl chloride, acetonitrile, rt, 24 h (compound 30) or (1) triethylamine, CH2Cl2, 0 °C, 5 min; (2) pivaloyl chloride, rt, 24 h (compound 31) or (1) Na, EtOH, rt; (2) EtOH, 50 °C, 15 min; (3) CHCl3, 50 °C, 30 min (compound 32) or 1N HCl, 2N KOH, potassium cyanate, rt, 2 h (compound 33) or (1) triethylamine, 1,1′-carbonyldiimidazole, rt, 30 min; (2) dimethylamine hydrochloride 80 °C, 6 h (compound 34); (d) 15% (m/m) palladium on activated carbon, H2, MeOH, rt, 24 h; (e) (1) carboxylic acid 2, CH2Cl2, 0 °C, 5 min; (2) 2-chloro-N-methylpyridinium iodide, DIPEA, rt, 24 h.