Cl.S1[CH2:8][CH2:7]CNCC1.CC[N:11]([CH:15]([CH3:17])C)[CH:12]([CH3:14])C.Cl[C:19]1[N:23]([CH3:24])[N:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26].[F-].[K+].CS(C)=[O:32]>O>[CH3:24][N:23]1[C:19]([N:11]2[CH2:12][CH:14]3[O:32][CH:17]([CH2:7][CH2:8]3)[CH2:15]2)=[C:20]([N+:25]([O-:27])=[O:26])[CH:21]=[N:22]11,4-Thiazepane hydrochloride (153 mg, 1 mmol) and DIPEA (0.26 mL, 1.5 mmol) were stirred in DMSO (4 mL) for 15 min at room temperature. 5-Chloro-1-methyl-4-nitro-1H-pyrazole (150 mg, 0.95 mmol) and potassium fluoride (170 mg, 3 mmol) were then added and the reaction mixture was heated at 70° C. for 18 h. The mixture was allowed to cool to room temperature and poured into water (4 mL). The aqueous was extracted with EtOAc (3×10 mL) and the combined organic layers were washed with brine (10 mL), separated, dried over MgSO4 and concentrated under reduced pressure to give 3-(1-methyl-4-nitro-1H-pyrazol-5-yl)-8-oxa-3-azabicyclo[3.2.1]octane (220 mg, 92%). This intermediate was dissolved in DCM (10 mL), cooled to 0° C., treated with m-chloroperbenzoic acid (400 mg, 1.9 mmol) and the resulting mixture stirred at room temperature for 16 hr. The resulting precipitate was filtered off washing with cold DCM (5 mL). The filtrate was washed with 2M NaOH (5 mL) and brine (5 mL), passed through a phase separation cartridge and concentrated under reduced pressure to give 4-(1-methyl-4-nitro-1H-pyrazol-5-yl)-1,4-thiazepane 1,1-dioxide (280 mg, 97% over two steps) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.14 (s, 1H), 3.87 (s, 3H), 3.59-3.55 (m, 2H), 3.41-3.36 (m, 6H), 2.29-2.24 (m, 2H).
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