2-Butenoic acid, 3-amino-, ethyl ester, (2Z)- → Ethyl 5-acetyl-2,6-dimethyl-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

HRID 1669760Notes

Reaction equation

HRID 1669760 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]=[C:13]([C:17](=O)[CH3:18])[C:14](=[O:16])[CH3:15])=[C:8]2[C:3]=1[C:4](=[O:21])[CH:5]=[C:6]([CH3:20])[O:7]2.[NH2:22]/[C:23](/[CH3:30])=[CH:24]\[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CC(O)C>[C:14]([C:13]1[CH:12]([C:9]2[CH:10]=[CH:11][C:2]([F:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:20])=[CH:5][C:4]3=[O:21])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:23]([CH3:30])[NH:22][C:17]=1[CH3:18])(=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 575033273-[(5-Fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Product 1

HCID 16045278Ethyl 5-acetyl-2,6-dimethyl-4-(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

150 mg (0.52 mmol) of 3-[(5-fluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione are dissolved with 33.6 mg (0.26 mmol) of ethyl 3-aminocrotonate in 5 ml of 2-propanol and heated under reflux under argon for 3 h. The solvent is removed in vacuo, and the residue is purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 2:1). 50.1 mg (48% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 3 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 2:1)

Sources & evidence

ORD record
ord-3c84be10aaf748ddb55af0c5685b8f2b
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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