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But-1-ene-1,3-dione → N-(4-((2-(-adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-oxobutanamide

HRID 56212
Notes
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Reaction equation

HRID 56212 reaction equation
[C:1]12([CH2:11][CH2:12][NH:13][C:14]3[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:15]=3[F:21])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:22]([CH:25]=[C:26]=[O:27])(=[O:24])[CH3:23]>CCOC(C)=O>[C:1]12([CH2:11][CH2:12][NH:13][C:14]3[CH:19]=[CH:18][C:17]([NH:20][C:26](=[O:27])[CH2:25][C:22](=[O:24])[CH3:23])=[CH:16][C:15]=3[F:21])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12642904But-1-ene-1,3-dioneHCID 131736912N1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamine

Product 1

HCID 90022560N-(4-((2-(-adamantan-1-yl)ethyl)amino)-3-fluorophenyl)-3-oxobutanamideYield 64.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N1-(2-(adamantan-1-yl)ethyl)-2-fluorobenzene-1,4-diamine (0.38 g, 1.32 mmol) in EtOAc (20 mL) was added acetyl ketene (0.22 g, 2.62 mmol) and the mixture was stirred at 90° C. overnight. The mixture was then cooled to rt and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=4:1) to give the title compound as a white solid (317 mg, 64%).

Workup

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

Sources & evidence

ORD record
ord-52580cd14e2a41c1a385092a05fc4b4f
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09434695B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes