2,6-Diethylaniline → HCID 178436232, compound

HRID 1406007Notes

Reaction equation

[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH2:5])[CH3:2].[Li]N([Si](C)(C)C)[Si](C)(C)C.[O:22]=[C:23]1[C:29]2[NH:30][N:31]=[C:32]([C:33](OCC)=[O:34])[C:28]=2[CH2:27][CH2:26][CH2:25][CH2:24]1>C1COCC1>[CH2:1]([C:3]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][CH3:11])[C:4]=1[NH:5][C:33]([C:32]1[C:28]2[CH2:27][CH2:26][CH2:25][CH2:24][C:23](=[O:22])[C:29]=2[NH:30][N:31]=1)=[O:34])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2,6-diethylaniline (0.106 mL, 0.66 mmol) in 5 mL of anhydrous THF under argon, 1M solution of LiN(TMS)2 in THF (0.660 mL, 0.66 mmol) at 0° C. was added dropwise. The mixture was stirred at 0° C. for 0.5 h then ethyl 8-oxo-1,4,5,6,7,8-hexahydrocyclohepta[c]pyrazole-3-carboxylate (0.050 g, 0.22 mmol) in 5 mL of anhydrous THF at 0° C. were added dropwise. Ice bath was removed and the mixture was stirred at room temperature for 1 h. Water (20 mL) was added and the mixture was extracted with AcOEt (2×30 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent evaporated to dryness. The crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8) to afford 0.055 g (80% yield) of the title compound.

Workup

customIce bath was removed
stirringthe mixture was stirred at room temperature for 1 h
additionWater (20 mL) was added
extractionthe mixture was extracted with AcOEt (2×30 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
customthe solvent evaporated to dryness
customThe crude solid was purified by flash chromatography on silica gel (eluant: AcOEt/hexane 2/8)

Sources & evidence

ORD record: ord-bfde6d121ee14566a8b8a02700707625
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916577B2

Reaction notes

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