[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:4]([CH3:16])[CH:3]=1.[Cl-].[NH4+]>C(O)C.O.[Zn]>[NH2:8][C:7]1[C:2]([Cl:1])=[CH:3][C:4]([CH3:16])=[C:5]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:6]=1A mixture of Intermediate 79A (175 mg, 0.66 mmol), zinc (432 mg, 6.61 mmol), ammonium chloride (354 mg, 6.61 mmol) in ethanol (10 mL) and water (5.0 mL) was heated to reflux for 30 min. The reaction mixture was concentrated, suspended in ethyl acetate and filtered. The filtrate was washed with water, aqueous NaHCO3 and brine, dried over MgSO4 and concentrated to give Intermediate 79 (149 mg, 96%) as a white solid. HPLC: Rt=0.453 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). MS (ES): m/z=235 [M+H]+. Intermediate 79 was used in the synthesis of Example 243.
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