Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[N:3]=1.[NH2:15][CH:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1.C(N(CC)C(C)C)(C)C.Cl.O1CCOCC1>CS(C)=O>[NH:19]1[CH2:20][CH2:21][CH:16]([NH:15][C:2]2[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[N:3]=2)[CH2:17][CH2:18]1A mixture of 2-[2-chloro-6-(trifluoromethyl)pyridin-4-yl]ethanol (0.085 g, 0.38 mmol, from Step 1), tert-butyl 4-aminopiperidine-1-carboxylate (0.30 g, 1.5 mmol) and N,N-diisopropylethylamine (0.16 mL, 0.94 mmol) in dimethyl sulfoxide (0.86 mL) was heated in the microwave to 100° C. for one hour, then to 140° C. for 140 minutes. The reaction mixture was concentrated. The residue was dissolved in 1,4-dioxane (2.8 mL) and was treated with 4.0 M hydrogen chloride in dioxane (2.8 mL, 11 mmol). After stirring overnight, solvent was removed in vacuo. Purification via preparative HPLC-MS (C18 eluting with a gradient of MeCN and H2O containing 0.15% NH4OH) afforded two major fractions, the desired product was the first eluting of the peaks having the desired mass (16 mg, 15%). LCMS (M+H)+: 290.1.
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