Dimethyl Sulfoxide → HCID 86680016, compound

Temperature

70 °C

8-Oxa-3-azabyclo[3.2.1]octane hydrochloride (150 mg, 1.0 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 hr. 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%). 1H NMR (400 MHz CDCl3) δ 8.04 (s, 1H), 4.43 (s, 2H), 3.86 (s, 3H), 3.73-3.70 (m, 2H), 2.61-2.58 (m 2H), 2.09-2.07 (m, 4H).

1. temperatureto cool to room temperature
2. extractionThe aqueous was extracted with EtOAc (3×10 mL)
3. washthe combined organic layers were washed with brine (10 mL)
4. customseparated
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure

ORD record

ord-bd726139d5f94d05b32dc4d11523692e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08614206B2