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. Author manuscript; available in PMC: 2011 Feb 26.

Published in final edited form as: J Med Chem. 2010 Oct 14;53(19):6867–6888. doi: 10.1021/jm1001748

Scheme 3a — ^a (a) 1-Methyl-1H-imidazole-4-sulfonyl chloride, DIPEA, CH₃CN, 0 °C → rt, 16 h, 95%; (b) 4-bromomethyl-N-(2-pyrimidinyl)-piperidine, Cs₂CO₃, DMF, rt, 4 d, 94%; (c) TFA-CH₂Cl₂-TIPS-H₂O, 47.5:47.5:2.5:2.5, rt, 1 h, 100%; (d) R⁴F, DIPEA, DMSO, 120 °C, 24–48 h, 48–97%; (e) (1) NaH, 0 °C, 30 min, (2) 5-chloromethyl-1-methyl-1H-imidazole 3 HCl,^29b 0 °C → rt, 2–3h, 63–96%.