Cyclobutyl 3-aminocrotonate → Cyclobutyl 5-acetyl-2,6-dimethyl-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

HRID 1669763Notes

Reaction equation

HRID 1669763 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]([CH:13]=[C:14]([C:18](=O)[CH3:19])[C:15](=[O:17])[CH3:16])=[C:8]2[C:3]=1[C:4](=[O:22])[CH:5]=[C:6]([CH3:21])[O:7]2.[NH2:23]/[C:24](/[CH3:33])=[CH:25]\[C:26]([O:28][CH:29]1[CH2:32][CH2:31][CH2:30]1)=[O:27]>CC(O)C>[C:15]([C:14]1[CH:13]([C:9]2[CH:10]=[C:11]([F:12])[C:2]([F:1])=[C:3]3[C:8]=2[O:7][C:6]([CH3:21])=[CH:5][C:4]3=[O:22])[C:25]([C:26]([O:28][CH:29]2[CH2:32][CH2:31][CH2:30]2)=[O:27])=[C:24]([CH3:33])[NH:23][C:18]=1[CH3:19])(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 57475512Cyclobutyl 3-aminocrotonateHCID 575033293-[(5,6-Difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione

Product 1

HCID 16045279Cyclobutyl 5-acetyl-2,6-dimethyl-4-(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)-1,4-dihydro-pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

80 mg (0.26 mmol) of 3-[(5,6-difluoro-2-methyl-4-oxo-4H-chromen-8-yl)methylene]pentane-2,4-dione are dissolved with 40.4 mg (0.26 mmol) of cyclobutyl 3-aminocrotonate in 2 ml of 2-propanol and heated under reflux under argon for 12 h. The solvent is removed in vacuo, and the residue is purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 1:2). 31.0 mg (27% of theory) of the title compound are obtained as a yellow solid.

Workup

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography (mobile phase: ethyl acetate/cyclohexane 1:2)

Sources & evidence

ORD record
ord-67a2f5bc72104bdb8bcb99e0560c8573
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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