Ethyl 2-(5-((Isopropylamino)methyl)-3-nitro-1H-pyrazol-1-yl)acetate → 5-Isopropyl-2-nitro-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one

HRID 407794Notes

Reaction equation

[CH:1]([NH:4][CH2:5][C:6]1[N:10]([CH2:11][C:12](OCC)=[O:13])[N:9]=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=1)([CH3:3])[CH3:2]>CO>[CH:1]([N:4]1[C:12](=[O:13])[CH2:11][N:10]2[N:9]=[C:8]([N+:17]([O-:19])=[O:18])[CH:7]=[C:6]2[CH2:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 151c (400 mg, 1.48 mmol) and methanol (30 mL) was stirred at 50° C. for 16h. The mixture was the concentrated under reduced pressure. The residue was diluted with water (80 mL) and extracted with ethyl acetate (3×50 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford 151d (300 mg, 90%) as a yellow solid. MS-ESI: [M+H]+ 225.3

Workup

concentrationconcentrated under reduced pressure
additionThe residue was diluted with water (80 mL)
extractionextracted with ethyl acetate (3×50 mL)
dry with materialThe combined organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-330024d150914e37a88d6bdbd174bcb6
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08754077B2

Reaction notes

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