But-1-ene-1,3-dione → N-(3-fluoro-4-((3-(tetrahydrofuran-2-yl)propyl)amino)phenyl)-3-oxobutan-amide

HRID 56220Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][O:14]1.[C:18]([CH:21]=[C:22]=[O:23])(=[O:20])[CH3:19]>CCOC(C)=O>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:22](=[O:23])[CH2:21][C:18](=[O:20])[CH3:19])[CH:5]=[CH:4][C:3]=1[NH:9][CH2:10][CH2:11][CH2:12][CH:13]1[CH2:17][CH2:16][CH2:15][O:14]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 2-fluoro-N1-(3-(tetrahydrofuran-2-yl)propyl)benzene-1,4-diamine (260 mg, 1.09 mmol) in EtOAc (10 mL) was added acetyl ketene (110 mg, 1.31 mmol) and the mixture was stirred at 80° C. overnight. The mixture was cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1) to give the title compound as yellow liquid (83 mg, 24%).

Workup

temperatureThe mixture was cooled to rt
concentrationconcentrated in vacuo
customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=2:1)

Sources & evidence

ORD record: ord-2597eddf038c410aaf1b84788b5a9f90
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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