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. 2020 Oct 15;11(12):2433–2440. doi: 10.1021/acsmedchemlett.0c00416

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© 2020 American Chemical Society

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Scheme 2 — Reagents and conditions: (a) corresponding acyl chloride, Et₃N, 1,4-dioxane, rt, 4 h; (b) H₂, 10% Pd/C, EtOH (for 8a and 8c) or MeOH (for 8b), rt, 24 h; (c) 3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride, pyridine, DCM; (d) 1 M NaOH, MeOH, rt, 24 h,; (e) 3,4-dichloro-5-methyl-1H-pyrrole-2-carbonyl chloride, toluene, reflux, 16 h; (f) SnCl₂·2H₂O, EtOH, reflux, 12 h; (g) ethyl oxalyl chloride, Et₃N, 1,4-dioxane, rt, 8 h (for the synthesis of 13); (g) Ac₂O, Et₃N, DCM, rt, 2 h (for the synthesis of 15a); or CDI, DMF, rt, 3 h; NH₃, rt, 16 h (for the synthesis of 15b); or nicotinic acid, EDC, NMM, HOBt, DMF, rt, 12 h (for the synthesis of 15c); or corresponding Boc-amino acid, EDC, NMM, HOBt, DMF, rt, 12 h (for the synthesis of 15d–e); (h) 4 M HCl, 1,4-dioxane, rt, 5 h.