Cl.Cl.[CH3:3][N:4]([CH3:12])[CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1.C(N(CC)CC)C.[F:20][C:21]([F:37])([F:36])[C:22]1[O:26][N:25]=[C:24]([C:27]2[S:31][C:30]([C:32](Cl)=[O:33])=[CH:29][CH:28]=2)[C:23]=1[CH3:35]>C1COCC1.CN(C=O)C>[CH3:3][N:4]([CH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:32]([C:30]2[S:31][C:27]([C:24]3[C:23]([CH3:35])=[C:22]([C:21]([F:36])([F:37])[F:20])[O:26][N:25]=3)=[CH:28][CH:29]=2)=[O:33])[CH2:7]1)[CH3:12]A solution of dimethyl-(S)-1-piperidin-3-ylmethyl-amine, dihydrochloride (Preparative Example 29, 108 mg, 0.5 mmol) in THF/DMF (3 mL/500 μL) was treated with triethylamine (95 μL, 1.0 mmol) followed by 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (74 mg, 0.25 mmol, as prepared in Example 2 Method B). The reaction mixture was vigorously stirred or 16 h then evaporated and diluted with water (5 mL). The crude reaction mixture was extracted with EtOAc (2×3 mL) which was then washed with a 1 N NaOH solution (2×3 mL), dried over MgSO4, filtered, and evaporated in vacuo to afford product as a colorless solid. The solid was dissolved in a EtOAc/hexanes (1:1) mixture (1 mL), filtered through a PTFE syringe filter, and again evaporated in vacuo to afford product as a colorless solid (31 mg, 31%). LC/MS 5.13 min, [M+1]+ 402.
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