But-1-ene-1,3-dione → N-(3-chloro-4-((2-methyl-1-(naphthalen-2-yl)propan-2-yl)amino)phenyl)-3-oxobutanamide

HRID 56224Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH3:23])([CH3:22])[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1.[C:24]([CH:27]=[C:28]=[O:29])(=[O:26])[CH3:25]>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:28](=[O:29])[CH2:27][C:24](=[O:26])[CH3:25])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([CH3:23])([CH3:22])[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 2-chloro-N1-(2-methyl-1-(naphthalen-2-yl)propan-2-yl)benzene-1,4-diamine (2.0 g, 6.16 mmol) in EtOAc (30 mL) was added acetyl ketene (1.55 g, 1.84 mmol) and the mixture was stirred at 90° 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)=1:1) to give the title compound as a white solid (2.00 g, 79%).

Workup

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

Sources & evidence

ORD record: ord-174d1e57cf63495fbcda1a3b04d8a5a9
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434695B2

Reaction notes

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