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Reagents and conditions: (a) tert-butyl (3-aminocyclo-hexyl)carbamate (mixture of diastereomers), DIEA, EtOH, 85 °C, 6 h; (b) 2-(methylthio)benzaldehyde, Na2S2O4, 1,4-dioxane/H2O (4:1), 80 °C, 24 h; (c) (i) TFA/DCM, overnight; (ii) 5-bromothiophene-2-carboxylic acid, HATU, DIEA, AcCN; (d) (i) 5-bromothiophene-2-carboxylic acid, HOBT, EDCI, TEA, DCM; (ii) TFA/DCM; (e) 4-fluoro-N-methyl-3-nitrobenzamide, DIEA, EtOH, 85 °C, 6 h.
