Hydrochloric Acid → HCID 58158497, compound

HRID 2095869Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-cyano-N-(3,4-difluorophenyl)acetamide (6.0 g, 30.6 mmol), (3E)-4-methoxybut-3-en-2-one (4.29 g, 42.8 mmol) and 2-(2-methoxyethoxy)ethanol (60 mL) was stirred at 90° C. for 20 min. 1,4-Diazabicyclo[2.2.2]octane (3.77 g, 33.6 mmol) was added, and the mixture was stirred at 125° C. for 5 hr. After cooling to room temperature, the mixture was adjusted to pH 5 with 2N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate/hexane (=1/1) and collected by filtration to give the title compound (3.69 g, 49%) as a pale-yellow solid.

Workup

stirringthe mixture was stirred at 125° C. for 5 hr
temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
customThe solvent was evaporated under reduced pressure
washthe obtained residue was washed with ethyl acetate/hexane (=1/1)
filtrationcollected by filtration

Sources & evidence

ORD record: ord-3faea6089baf467384f2512ad03d2fb7
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445509B2

Reaction notes

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