Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([CH:10]([NH2:13])[CH2:11][NH2:12])[CH:7]=[CH:8][CH:9]=1.[OH-:14].[Na+].[O:16]1[CH2:22][C:21](=O)[CH2:20][O:19][CH2:18][CH2:17]1.[CH:24](Cl)(Cl)Cl.Cl>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[F:3][C:4]1[CH:5]=[C:6]([CH:10]2[NH:13][C:24](=[O:14])[C:21]3([CH2:22][O:16][CH2:17][CH2:18][O:19][CH2:20]3)[NH:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=10.47 g (2.1 mmol) 1-(3-fluorophenyl)ethan-1,2-diamine dihydrochloride were placed with 23 mg (0.10 mmol) benzyltriethylammonium chloride in 50 ml dichloromethane and cooled with ice/acetone. Then 0.71 ml (14 mmol) of a 50% sodium hydroxide solution were added. At 0° C. 0.23 g (2 mmol) [1,4]dioxepan-6-one were added dropwise together with 0.24 ml (4.6 mmol) chloroform and 20 ml dichloromethane. The mixture was left overnight to warm up to RT. Then the reaction mixture was cooled to 0° C. and adjusted to pH 1 with a 6N aqueous hydrochloric acid solution. The phases were separated. The aqueous phase was made alkaline with a 4N sodium hydroxide solution and extracted with DCM. The combined organic phases were dried and evaporated to dryness by rotary evaporation.
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