1-Methyl-3-aminopyrazole → 1-(1-methyl-1H-pyrazol-3-yl)-2-oxopyrrolidine-3-carbonitrile

HRID 632770Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH2:7])=[N:3]1.[C:8]([C:10]1([C:13](OCC)=[O:14])[CH2:12][CH2:11]1)#[N:9]>COC1CCCC1.C(OCC)(=O)C>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([C:8]#[N:9])[C:13]2=[O:14])=[N:3]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-methyl-1H-pyrazol-3-amine (223 mg) in cyclopentyl methyl ether (5.0 mL) was added ethyl 1-cyanocyclopropanecarboxylate (0.90 ml). The reaction mixture was stirred at 120° C. for 30 hr, and diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (237 mg).

Workup

washThe diluted solution was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a0e77610c0bd4d10bae8a39ec29f4fdf
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321757B2

Reaction notes

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