[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](N)[CH:8]=2)[N:3]=1.N([O-])=O.[Na+].[S:17](=[O:19])=[O:18].FC1C=CC([C@H](NC(C2CCC(NS(C3C=CC4N=C(C5C=CC=CC=5)OC=4C=3)(=O)=O)CC2)=O)C)=CC=1.[ClH:57]>C(O)(=O)C.O.[Cu](Cl)Cl>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:17]([Cl:57])(=[O:19])=[O:18])[CH:8]=2)[N:3]=12-Chloroquinolin-6-amine (6.45 g, 36.1 mmol) was dissolved in acetic acid (50 mL) and hydrochloric acid, 37% (14 mL) and cooled to 0° C. A solution of sodium nitrite (2.74 g, 39.7 mmol) in water (8 mL) was then added dropwise, and the reaction mixture was then stirred at 0° C. for 15 min. the entire reaction mixture was then poured into a 0° C. solution of sulfur dioxide, copper(II) chloride and acetic acid (1 L, 36.1 mmol; solution prepared as described for Example 11). The reaction mixture was allowed to warm to room temperature overnight. LC-MS at this time showed reaction had progressed to completion. The reaction mixture was then concentrated, and the residue was partitioned between ethyl acetate and water. The aqueous phase was back extracted, and the combined organic phases were dried over MgSO4, filtered and concentrated to afford a creamy orange solid, which was dried under high vacuum to provide 8.21 g (87% yield) of product.
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