Dimethyl Sulfoxide → 5-(1-Methoxypropan-2-yl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

HRID 1022164Notes

Reaction equation

Br[CH2:2][CH2:3][N:4]1[C:8]([CH2:9]Cl)=[CH:7][C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.[CH3:14][O:15][CH2:16][CH:17]([NH2:19])[CH3:18].CS(C)=O>O>[CH3:14][O:15][CH2:16][CH:17]([N:19]1[CH2:2][CH2:3][N:4]2[N:5]=[C:6]([N+:11]([O-:13])=[O:12])[CH:7]=[C:8]2[CH2:9]1)[CH3:18]

Participants

Conditions

Temperature: 120 °C

Procedure

A microwave vial equipped with a magnetic stirrer was charged with 1-(2-bromoethyl)-5-(chloromethyl)-3-nitro-1H-pyrazole 296c (1.0 g, 3.7 mmol), 1-methoxypropan-2-amine (1.0 g, 11.2 mmol), and DMSO (6 mL). The mixture was heated at 120° C. under microwave irradiation for 1.0 h. It was the cooled to room temperature and diluted with water (30 mL). The resulting mixture was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with petroleum ether/ethyl acetate (60/1 to 1/1) to afford 300a (600 mg, 68%) as a yellow solid. MS-ESI: [M+H]+ 241.0

Workup

customA microwave vial equipped with a magnetic stirrer
temperaturecooled to room temperature
extractionThe resulting mixture was extracted with ethyl acetate (3×20 mL)
customThe combined organic layer was dried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica-gel column chromatography
washeluting with petroleum ether/ethyl acetate (60/1 to 1/1)

Sources & evidence

ORD record: ord-9543b2bc21f84f6fa8469a43e6531d96
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716274B2

Reaction notes

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