But-1-ene-1,3-dione → N-(3-fluoro-4-(3-oxomorpholino)phenyl)-3-oxobutanamide

HRID 56288Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[C:4]([F:15])[CH:3]=1.[C:16]([CH:19]=[C:20]=[O:21])(=[O:18])[CH3:17]>CCOC(C)=O>[F:15][C:4]1[CH:3]=[C:2]([NH:1][C:20](=[O:21])[CH2:19][C:16](=[O:18])[CH3:17])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][C:9]1=[O:14]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(4-amino-2-fluorophenyl)morpholin-3-one (2.51 g, 11.9 mmol) and acetyl ketene (2.51 g, 29.9 mmol) in EtOAc (40 mL) was stirred at 80° C. for 24 h. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:4) to give the title compound as a yellow solid (2.15 g, 61%).

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:4)

Sources & evidence

ORD record: ord-b3862ce897db4dd98957ca235176814c
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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