[CH:1]1([C:4]2[C:5]([N:27]3[CH2:32][CH2:31][CH2:30][C@H:29]([NH:33]C(=O)OC(C)(C)C)[CH2:28]3)=[N:6][C:7]([N:10]3[C:18]4[CH:17]=[C:16]([C:19]5[CH:20]=[N:21][CH:22]=[C:23]([CH2:25][CH3:26])[CH:24]=5)[N:15]=[CH:14][C:13]=4[CH:12]=[N:11]3)=[CH:8][CH:9]=2)[CH2:3][CH2:2]1.Cl>CO.O1CCOCC1>[CH:1]1([C:4]2[C:5]([N:27]3[CH2:32][CH2:31][CH2:30][C@H:29]([NH2:33])[CH2:28]3)=[N:6][C:7]([N:10]3[C:18]4[CH:17]=[C:16]([C:19]5[CH:20]=[N:21][CH:22]=[C:23]([CH2:25][CH3:26])[CH:24]=5)[N:15]=[CH:14][C:13]=4[CH:12]=[N:11]3)=[CH:8][CH:9]=2)[CH2:3][CH2:2]1To a solution of tert-butyl N-[(3S)-1-[3-cyclopropyl-6-[6-(5-ethyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.0597 mmol; 32.2 mg) in Methanol (10 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 139 as an off-white solid (20 .mg, 7.4%). MS (ESI) m/z: 440.3 [M+H]+
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