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Synthesis of sulfonamide isosteres 18 and 19: a) iBuNH2, iPrOH, 65°C; b) 14, CH2Cl2, Et3N, 23°C, (87% over two steps for 15b and 95% over two steps for 15c); c) Ph3P, THF/H2O (3:1), 23°C; d) Boc2O, THF/H2O (1:1), NaHCO3, 23°C (83% over two steps for 16b and 70% over two steps for 16c); e) mCPBA, CH2Cl2, 23°C; f) cyclopropylamine, THF, 65°C, (97% over two steps for 18 and 98% over two steps for 19); g) TFA, CH2Cl2, 0°C.
