[F:1][C:2]([F:18])([F:17])[C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:4]=1.CN(C(F)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:34][C:35]1[CH:40]=[C:39]([NH2:41])[CH:38]=[CH:37][N:36]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][C:35]1[CH:40]=[C:39]([NH:41][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([C:5]3[N:4]=[C:3]([C:2]([F:1])([F:18])[F:17])[O:7][N:6]=3)=[CH:16][CH:15]=2)[CH:38]=[CH:37][N:36]=1To compound 12b, 4-(5-trifluoromethyl-[1,2,4]oxadiazol-3-yl)-benzoic acid, (40 mg, 0.155 mmol) in DMF (516 μL) was added TFFH (82 mg, 0.310 mmol), 2-methylpyridin-4-amine (33.5 mg, 0.310 mmol) and DIPEA (81 μL, 0.465 mmol). The reaction was stirred at 50° C. for 1.5 h. The reaction mixture was subjected to purification by reverse phase prep-HPLC (gradient elution, water/MeCN both containing 0.1% TFA). Fractions containing the desired compound were combined and freeze-dried. The resulting material was dissolved in a mix of ACN/MeOH. They were loaded on a PL-HCO3 MP cartridge (from StratoSpheres™ SPE) and eluted with ACN (3 ml). The eluate was diluted with water (10 ml) and freeze-dried to yield the final compound.
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