[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:8]([O:10]C)=[O:9])[CH3:3].O.[OH-].[Li+]>O1CCCC1.O>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([F:15])[CH:14]=1)[C:8]([OH:10])=[O:9])[CH3:1]Methyl 3-[(dimethylamino)methyl]-5-fluorobenzoate (0.040 g, 0.19 mmol from Step 3) was dissolved in tetrahydrofuran (3 mL) and lithium hydroxide monohydrate (0.0954 g, 2.27 mmol) dissolved in water (1 mL) was added. The reaction was stirred for 3 hours. The crude reaction mixture was purified by preparative HPLC-MS (C18, eluting with a gradient of H2O/MeCN containing 0.15% NH4OH). The eluent containing the desired mass was evaporated using rotary evaporation to afford product (22 mg, 59%), which was used directly in Step 5. LCMS (M+H)+: 198.1.
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