[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]2[N:15]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[C:18]([F:26])[CH:17]=3)[C:13]([NH2:27])=[N:12][CH:11]=2)[CH2:5]1)(=[O:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.CO>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH:6]([C:10]2[N:15]=[C:14]([C:16]3[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[C:18]([F:26])[CH:17]=3)[C:13]([NH2:27])=[N:12][CH:11]=2)[CH2:5]1)(=[O:3])[CH3:2]To a mixture of methyl 4-(6-(1-acetylpiperidin-3-yl)-3-aminopyrazin-2-yl)-2-fluorobenzoate (50 mg, 0.134 mmol) in THF (4 mL) and MeOH (2 mL) was added 1 M LiOH (0.500 mL, 0.500 mmol). The reaction mixture was stirred at room temperature for 4 h. The pH of reaction mixture was adjusted to ˜3 with 2 N HCl, and the product was extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was proceeded for next step without purification (34 mg, 70.7%). LCMS (m/z): 359.1 (MH+), 0.534 min.
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