[CH:1]1([N:4]2[C:8]3[C:9]([O:25][C@@H:26]([C@H:28]4[CH2:32][NH:31][C:30](=[O:33])[CH2:29]4)[CH3:27])=[N:10][C:11]([C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]5)=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.FC(F)(F)S([O:46][CH2:47][C:48]([F:51])([F:50])[F:49])(=O)=O>C(Cl)Cl>[CH:1]1([N:4]2[C:8]3[C:9]([O:25][C@@H:26]([C@H:28]4[CH2:32][NH:31][C:30](=[O:33])[CH2:29]4)[CH3:27])=[N:10][C:11]([C:13]4[CH:18]=[CH:17][C:16]([N:19]5[CH2:24][CH2:23][N:22]([CH2:47][C:48]([F:51])([F:50])[F:49])[CH2:21][CH2:20]5)=[CH:15][CH:14]=4)=[CH:12][C:7]=3[N:6]=[CH:5]2)[CH2:2][CH2:3]1.[F:49][C:48]([F:51])([F:50])[C:47]([OH:25])=[O:46]In an appropriate sized vial the trifluoroacetic acid salt (R)-4-((R)-1-((3-cyclopropyl-6-(4-(piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.42 (25 mg, 0.046 mmol) and triethylamine (27 mg, 0.27 mmol) were dissolved in DCM (1.5 mL). To this mixture 2,2,2-trifluoroethyl trifluoromethanesulfonate (12 mg, 0.053 mmol) was added and the mixture was stirred at room temperature for 24 h. The mixture was concentrated under reduced pressure and the residue was purified via prep HPLC (2-65% acetonitrile in water, 0.1% trifluoroacteic acid) to provide (R)-4-((R)-1-((3-cyclopropyl-6-(4-(4-(2,2,2-trifluoroethyl)piperazin-1-yl)phenyl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one 3.47 as its trifluoroacetic acid salt.
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