[F:1][C:2]([F:11])([F:10])[C:3]1[N:4]=[C:5]([C:8]#[N:9])[S:6][CH:7]=1.CO[Na].[NH4+:15].[Cl-]>CO.C(Cl)Cl>[F:11][C:2]([F:1])([F:10])[C:3]1[N:4]=[C:5]([C:8]([NH2:15])=[NH:9])[S:6][CH:7]=1To a solution of compound 285b (28.12 g, 1.0 eq.) in MeOH (13 mL) in an ice/water bath was added MeONa (853 mg, 0.1 eq.) portionwise. The reaction mixture was stirred in the ice/water bath for 15 min and at room temperature for 1 hr. NH4Cl (16.88 g, 2.0 eq.) was then added and the mixture was stirred at room temperature for 4 days. Solvent was removed in vacuo. The solid obtained was suspended in DCM (60 mL) and recovered by filtration. The solid was suspended in MeOH (50 mL) and filtered. The filtrate was concentrated under reduced pressure to yield compound 285 as a white solid in 32% yield. MS (ESI, EI+): m/z=196 (MH+).
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