Diethylene Glycol Monomethyl Ether → HCID 66968998, compound

HRID 2095803Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:14])[CH2:11][C:12]#[N:13].CO/[CH:17]=[CH:18]/[C:19](=O)[CH3:20].N12CCN(CC1)CC2.COCCOCCO>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:19]([CH3:20])=[CH:18][CH:17]=[C:11]([C:12]#[N:13])[C:10]1=[O:14]

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of N-(2-bromo-4-fluorophenyl)-2-cyanoacetamide (5.00 g, 19.4 mmol), (3E)-4-methoxybut-3-en-2-one (2.33 g, 23.3 mmol), 1,4-diazabicyclo[2.2.2]octane (2.18 g, 19.4 mmol) and 2-(2-methoxyethoxy)ethanol (50 mL) was stirred at 130° C. for 5 hr. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with 1N hydrochloric acid, water (×2) and saturated brine, dried over anhydrous magnesium sulfate, and filtered through a silica gel pad. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (100 g, ethyl acetate/hexane=2/98→50/50), washed with ethyl acetate-hexane and collected by filtration to give the title compound (1.78 g, 29%) as a pale-brown powder.

Workup

temperatureAfter cooling to room temperature
washwashed with 1N hydrochloric acid, water (×2) and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered through a silica gel pad
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by silica gel column chromatography (100 g, ethyl acetate/hexane=2/98→50/50)
washwashed with ethyl acetate-hexane
filtrationcollected by filtration

Sources & evidence

ORD record: ord-2c39a94744494f8e817a16ca418aac6b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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