[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH2:12])[CH:6]=[CH:5]2.Cl[CH2:14][C:15](=O)[CH3:16].C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1.O>[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:14]=[C:15]([CH3:16])[N:12]=[C:7]1[CH:6]=[CH:5]26-Iodo-quinolin-2-ylamine (270 mg, 1.0 mmol), chloroacetone (111 mg, 1.2 mmol), sodium bicarbonate (252 mg, 3.0 mmol), and catalytic tetrabutylammonium iodide were dissolved in 1,4-dioxane and water, and stirred at 80° C. overnight. The reaction was cooled to room temperature and concentrated, and the residue was purified by preparative HPLC to give the desired compound, 1m.
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