Dimethylformamide dimethyl acetal → HCID 67404651, compound

HRID 910248Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[N:9]1[C:10]([C:18]2[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=2)=[CH:11][N:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=12>CN(C)C=O>[CH3:6][N:4]([CH3:5])/[CH:3]=[CH:25]/[C:24]([C:21]1[CH:22]=[CH:23][C:18]([C:10]2[N:9]=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[CH:11]=2)=[CH:19][CH:20]=1)=[O:26]

Participants

Conditions

Temperature: 120 °C

Procedure

Subsequently, N,N-dimethylformamide dimethyl acetal (3.0 mL) was added to a solution of 1-(4-imidazo[1,2-a]pyridin-2-ylphenyl)-1-ethanone (2.13 g) in N,N-dimethylformamide (50 mL), followed by heating at 120° C. for 8 hours. The reaction mixture was cooled to room temperature, and the precipitated solid was recovered through filtration, followed by washing with ethanol. The filtrate was concentrated under reduced pressure. The thus-obtained solid and the residue were subjected to flash chromatography. Fractions eluted by dichloromethane-methanol (30:1) were concentrated under reduced pressure, and the solid was recovered through filtration by use of ethyl acetate. Through the above procedure, (E)-3-dimethylamino-1-(4-imidazo[1,2-a]pyridin-2-ylphenyl)-2-propen-1-one (2.38 g) was yielded.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationthe precipitated solid was recovered through filtration
washby washing with ethanol
concentrationThe filtrate was concentrated under reduced pressure
washFractions eluted by dichloromethane-methanol (30:1)
concentrationwere concentrated under reduced pressure
filtrationthe solid was recovered through filtration by use of ethyl acetate

Sources & evidence

ORD record: ord-3e0c21cf91ca4c4f982c4473d1c8fe1c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022075B2

Reaction notes

Loading…